Humility & Truth Seeking

I've always placed a lot of value on people who are humble. I've written about it here. I've always thought about humility in the context of getting better at what you do. If you have the humility to know that you aren't the best at everything, that drives you to improve. And of course it makes you much more fun to work with. 

I had a conversation with someone the other day who pointed out another reason why humility is such a great attribute: it's a signal that you see the world clearly. If you have the humility to see your weaknesses (which we all have) and to understand that whatever success you've had required the support of lots of luck and lots of support from other people, then you see the world more clearly than someone that doesn't. And an undervalued skill in the workplace is the ability to see the world clearly. To seek the truth.

An executive's job is to make good decisions. You can't make good decisions if you're not seeing the world as it is. Being able to see the world as it is might be the most important thing an executive can do. Often once you know the truth, making the decision is often the easy part. Humble people are naturally better at this. and this is just another reason why that value is so important in the workplace. 

Investor Context & Incentives

The best managers prioritize giving their teams as much context as possible. When employees lack context, it leads to an enormous amount of unnecessary friction and uncertainty. It’s crucial for managers to give context around the work they’re asking employees to do, the decisions they’re making, and the priorities they’re driving. At the same time, employees should play a role here as well. If they’re not getting the context they need from their manager, they should ask. Employees should empathize and push hard to get in the head of their manager and understand their manager’s incentives and the context they’re operating in. It’s a partnership.

While this is fairly well understood, often, I find that managers don’t understand the context and incentives of their boss’s boss or even their boss’s boss’s boss (the company’s investors). I’ve found that deeply understanding how investors think is an essential part of being an effective operator. It’s even helpful to understand the content and incentives of a company’s investors’ bosses (the investors’ limited partners).

Here are four books that have helped me get inside the heads of the individuals that invest in the companies I’ve worked with, both venture-backed and private equity-backed. Understanding the history of these industries, their investment strategies, and how investors are measured and managed has made me a much more effective operator and leader.

Venture Capital

The Power Law: Venture Capital and the Making of the New Future by Sebastian Mallaby

Angel Investing: The Gust Guide to Making Money and Having Fun Investing in Startups by David Rose

Private Equity

The Private Equity Playbook: Management’s Guide to Working with Private Equity by Adam Coffey

Two and Twenty: How the Masters of Private Equity Always Win by Sachin Khajuria

Refusing To Fail

I heard Phil Mickelson, the legendary golfer, tell a great story the other day.

He was asked what makes the best golfers the best golfers in the world. He told a story about how a long time ago, he really struggled with short putts. One day his coach recommended that he try to make 100 three-foot putts in a row. If he missed one, he'd have to start all over again. And he should keep practicing this until he can reliably make 100 in a row. He claims that one time he made it all the way to 99, missed the 100th, and started over. 

Years later, he was mentoring an up-and-coming amateur golfer who was struggling with short putts, and he gave that golfer the same advice. Several months later, he checked in on how the golfer was doing with his putting, and the golfer said, "yea, that was really hard, I got to where I could make about 50 in a row, and I gave up.”

This golfer never made it in the PGA.

This is a great analogy when thinking about startup investing. Often, in the early days, you're really investing less in the idea or the product or the market; you're really investing in the founder themselves and their willingness to persevere and navigate through the idea maze and do what, in some cases, seems impossible. Some people work on some projects where for whatever reason, they will absolutely refuse to fail. Elon Musk is a great example. Both SpaceX and Tesla should've failed multiple times. But he persevered and forced it to happen through sheer will. Of course, he's incredibly smart and talented, but that wouldn't have been nearly enough. This quality doesn't exist in everyone, and even for those that do, it doesn't exist for every project at every time in their lives, given changing life circumstances and priorities.

This golf analogy is a good one to consider when you're investing at an early stage where you don't have much to go on other than the talents, skills, and dedication of the founder and founding team.

Learning How To Learn

Perhaps the most valuable skill one can have today is the ability to learn new things. The world is changing so fast. Static, top-down learning and development programs are quickly becoming outdated and irrelevant. 

The good news is that there is so much information available for free. Any self-motivated individual can learn almost anything on their own — assuming they know how to learn in a self-directed way.

In my mind, there are three steps to being proficient at self-directed learning:

1/ Identify what you don't know that's important to learn.

2/ Find resources to learn about the things you don't know.

3/ Do the work to learn about the things you don't know. 

Identify what you don't know. This is the hardest part. Because often you don’t know what you don’t know. This is where it's helpful to have mentors that can help identify your blind spots. It's also helpful to have a network of other people who are doing your job or the job you want to do. 

For an aspiring sales leader, here’s a list of things they should be learning as they climb the ladder from individual contributor to a sales manager to an executive.

Individual Contributor:

Sales tactics (discovery, outreach, access, presenting, proposals, objection handling, creating urgency, closing, etc.).

Understanding your buyer and your buyer's industry (business model, competitors, motivations, priorities, org chart, decision framework, regulatory, etc.).

Sales Manager:

Management (hiring, firing, employee engagement, giving feedback, setting priorities, territory management, performance management, etc.).

Sales strategy (forecasting, OKR management, customer segmentation, prioritization, leadership reporting, etc.).

Executive:

Management against industry metrics (e.g. in SaaS - CAC/LTV, Rule of 40, Payback period, growth rates, gross margins, etc.). 

Company strategy. Setting mission and vision. High-level qualitative goals and financial goals. 

Thinking like an investor. Understanding how financial metrics, storytelling, and a long-term plan connects to a company’s valuation. Understanding the mindset and motivation of investors that would invest in your company. 

Find resources. This is relatively easy these days. Use Twitter to follow experts in your areas of interest. Setup a Feedly account to get a feed of blog posts related to the interest area. Setup your podcast feed to receive daily podcasts on the topic. Read the best books on the topic. Join communities (such as Pavillion or SaaStr) to interact with peers. Leverage your investor networks (First Round Capital has a great one). Find a coach. Find a mentor.

Do the work. Once you've identified the learning area, start to obsess about it and immerses yourself in content. You'll quickly identify areas that you didn't know you didn't know. Learn about those things. Create habits that force you to keep learning. Listen to one podcast per day. Read 50 pages per day. Set a goal of having coffee with at least one mentor or person that does the job you want to do each month. Repeat. 

Employee Stock Options & Funding Rounds

A friend of mine sent a link to a press release about a company that just closed a huge funding round at a huge valuation that expects to go public over the next few years. He wanted my thoughts on other companies that he could join that have had similarly successful funding rounds. His thinking was that he could make a lot of money on the next few financing events, even an IPO.

I think job searchers need to be careful with this kind of thinking. A successful funding round with great investors is a very positive signal. And it's always tempting to jump on the latest rocket ship. But there are a few things potential employees should consider before joining a company following a large funding announcement:

You're not going to get credit for the company's past success. If a company raises a Series B round at a $100M valuation, following a $10M Series A round, the company's valuation has grown by 10x. That's a lot of value creation. But if you join the company after the Series B has closed, you've missed out on all of it. The stock options you receive will be priced at the post Series B valuation. So you're starting from zero. You'll only get credit for the value you create going forward. You have to place a bet on the company's ability to continue to build value on top of what they've already created. A small caveat here: there's often a difference between the valuation investors paid and the company's fair market value, as determined by auditors. So employees that come in after the round might not pay as much as investors paid.

Valuations are super high right now. Because private company valuations are typically marked against the public market, and the public markets are on a 12-year bull run, valuations are arguably inflated at the moment. If the bull market continues, this isn't a problem. But if prices come back down to earth, valuations could come down, and you may find that your options are underwater (meaning they're worth less than the price you'll have to pay for them). 

The later you join, the less equity you'll get. Startups reward early employees with lots of equity (potential upside) in return for taking the risk of joining before anything has been built. As time goes on, this risk decreases, and so does the amount of equity the company needs to grant to attract great people. Less risk typically means less equity.

The less senior you are, the less equity you'll get. Generally, the really material stock option grants (.5% to 2% of the value of the company) are reserved for the most senior executives. Employees at lower levels will receive a fraction of that.

Your options have to vest. In most cases, you won't just get an equity grant. You'll have a vesting schedule. Typically over four years with a 1-year cliff. Meaning you won't have the right to buy your options unless you've been at the company for more than a year. 

Your vested options aren't liquid. Not only do you have to create value on top of the last funding round, but you also have to find a way to cash out at some point. Generally, this is only done through an acquisition, a secondary offering where an investor buys some amount of employee shares, or an IPO. While IPOs have made a resurgence, it's enormously rare that a startup makes it that far; of the tens of thousands of startups out there, less than 200 companies went public in 2019. 

With all of this said, don't get me wrong, funding rounds are an exciting thing. And they're absolutely a signal that the company is onto something. And I’m a huge fan of investing in private companies as early as possible. My point is that potential employees should act like an investor and dig deep on how much value they believe can be created following the big announcement, and what share of that value they'll receive, and the likelihood that that value will be liquid within a reasonable time frame. 

This is particularly important for salespeople as they negotiate job offers. There's a tradeoff associated with optimizing for your own success (cash from commission) versus the success of the larger organization (equity). Depending on the circumstances, one can be a lot bigger than the other. The above considerations are important inputs into how to think about the company you might want to join and the compensation plan you want to advocate for as you negotiate an offer.

Leverage

 
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Over the weekend I read the Almanack of Naval Ravikant. Naval is an investor and entrepreneur and the founder of AngelList. The book gives his unique perspective on building wealth and enjoying life.

I flew through this book. I literally couldn’t put it down. The part I enjoyed the most was his perspective on leverage. He believes that leverage is the thing that leads to wealth. You can get leverage from people working for you. You can get leverage from investing your money. But the highest form of leverage — the new form of leverage — is to spend time selling or building products with no marginal cost of replication. This is easy to do in the digital age. You can write some code that can create infinite value, well beyond the time you put into writing the code. You can create a podcast that millions of people can listen to. These are things where the output is disconnected from the input. This blog post is a form of this leverage. It only took me a few minutes to write, but it can be read by millions of people for years to come.

As Naval points out in the book:

A general contractor has more leverage than the person that repairs the house.

A real estate developer has more leverage than the general contractor.

A money manager of a real estate investment fund has more leverage than the real estate developer.

Zillow has more leverage than all of them.

You see that as you climb the ladder, the value created gets more and more disconnected from the input. Zillow, in addition to having labor-based leverage (employees) and money-based leverage (venture capital), also has code-based leverage (leverage that can scale infinitely with near-zero marginal cost). Whereas the person repairing the house has none of that. That person is paid an hourly wage that is tied perfectly to the amount of time he or she puts in.

I really like this way of thinking about modern-day wealth creation. Spend your time on high leverage activities and projects, particularly those that are digitally-oriented. This is one thing I think people miss when they point to tech stocks being overvalued. These companies can get really big really quickly. That can be hard to wrap your head around.

The full excerpt on leverage can be found here. I highly recommend giving it a read.

Some Notes on Managing People

Earlier this week, my team went through a day and a half management training. It surfaced a bunch of things that I've learned about managing people over the last several years. I made some notes and thought I'd share them here.

1/ Some managers see their role as being the one that needs to smooth things over. This is the wrong approach. As Karl Marx said, it's best to "sharpen the contradictions." Bring the conflict up to the surface so everyone can see it and deal with it.

2/ When managing managers, sometimes the most important thing you can do is help them make the hard decisions they already know they need to make. Give them the support, safety, and clarity to execute on the hard stuff.

3/ Self-awareness and general awareness are two of the most crucial attributes of a leader. You have to know how you're being perceived and you have to know the issues on the team. You have to be in touch with the 'water cooler talk'. You have to make sure people understand that you know what's going on in their worlds. A clueless leader is the worst kind of leader.

4/ Create a habit of regularly expressing unsolicited gratitude to your reports. This is rocket fuel from an engagement and loyalty perspective.

5/ Use the writer/editor analogy when thinking about how much leverage you're getting from your reports. If you're doing a lot of writing, you're not getting enough leverage.

6/ Giving feedback is a muscle. When you do it a lot, it's easy. When you don't do it a lot, it's hard. Make giving feedback a regular part of the way you interact with your team.

7/ In a conflict, try to understand the other person's argument so well that you can make their argument for them with more clarity than they can. Don't make your argument until you can do this.

My User Guide

Several months ago, my company’s CEO, Jay Desai, was featured in the First Round Review in a piece titled The Indispensable Document for the Modern Manager. The feature was about Jay’s “user guide” that he had written for his team that outlines the way he works and how his team can work with him most effectively.

From the piece

 
He’s seen too many immensely talented and productive teams stall because of a subtle misunderstanding on how to best work with each other. After consecutive year-long searches for his Head of Product and Head of Operations, he didn’t want to squander that investment because he couldn’t figure out how to work with them.

So what did Desai do? He penned a user guide — similar to the kind that’d accompany a rice cooker or bassinet — but this one deconstructed how he operated optimally, when he might malfunction, and how others could use him to their greatest success.
 

This guide has been a great help to Jay’s direct reports and many others across our company.

As the piece mentions, Jay inspired me to write my own user guide.

I’ve found it to be invaluable — especially for my newer hires. Rather than taking several months to figure me out they can cut right to the chase and get lots of context on how to quickly start working together most productively.

I highly recommend writing a user guide and sending it to your team and asking them to do the same.

See my user guide below. I’ve embedded it as a Google Doc so any changes I make to it will flow through to this post.

Writing To Learn

Tim Ferris had a great podcast with Daniel Pink a couple weeks ago. I'm a big Daniel Pink fan. I highly recommend reading his book To Sell Is Human

In the podcast, Daniel talks about the fact that one of the main reasons he writes is not to teach people something but rather for him to learn something. And often, when he sits down to write about an idea part of the way into it he realizes that the idea stinks. Or that the theory he set out to write about is just wrong.

This really resonated with me. The reason I've kept writing on this blog for more than ten years isn't to tell people things I know that they don't (though if that happens that's great). The primary reason is that I learn through writing more than other medium. If I have an idea or a theory I find it enormously valuable to get it down on paper. I'm no different than Daniel in that I have literally dozens of draft blog posts in my Squarespace account that I haven't published because halfway through writing them I realized the idea wasn't good or was wrong or wasn't fully baked. 

I highly recommend that people write down their ideas on a blog or an Evernote or a personal journal. Writing forces you to focus and think clearly and consider alternatives and ensure that an idea isn't just a whim but a well thought out, actionable concept that matters. The clarity that comes from writing is invaluable.

For me, that clarity has been the best thing about writing on this blog.

How To Know You're Hiring Great People

Recently someone asked me how I get comfortable that I'm hiring great people. Obviously there’s a ton of work that goes into making a hire so I won’t go into all of the detail. But just before I’m ready to pull the trigger there are four checkpoints I use to make sure I’m making the right call.

  1. I can clearly point to something about them (beyond functional expertise) that they can do (or I believe they will be able to do) at a world-class level.
  2. Credible, smart, successful people say amazing things about them.
  3. If I strip away their credentials, I'm still really fired up about making the hire
  4. The reason they bounced from one job to the next doesn’t concern me, it inspires me.

There are obviously lots of other things I could add to this list but I’ve found that I'm generally making a great hire when these four things are in place.

Four Productivity Apps

Here are four apps that I've been using recently that have increased my productivity.

Accompany. This app will scour your calendars and see who you're meeting with in the coming days and weeks and will build out a profile for each person that includes news mentions, bios listed on the web and updates from their presence on Twitter, AngelList, Crunchbase, LinkedIn and other social networks. It pulls everything into a one-page profile. Just prior to your meeting it will send you an email with all of these details. Last week I was at the HIMSS conference in Las Vegas and found it invaluable. As I walking between meetings I could read through the manifest for my next meeting and get a refresh on who I was about to talk to. Following the meeting it adds the people you've met to your network and it will continue to push out updates. You can set preferences so you only get updates on people you want to hear about. 

MobileDay. I’ve been using this one for a while but just started using it more often. MobileDay scours your calendars for upcoming conference calls and pulls the conference call dial-in details into the app and pushes you a notification just prior to the meeting so that you can dial into the call with just one click. You just literally just click on the notification and it will dial you in. This is so much better than switching between my calendar app and phone app trying to remember a ten digit number to get dialed in.

Brain.fm is an app that has ambient sounds on a timer that helps with intense focus. I often listen to music when I'm writing but I've found that if I really need to focus on something for a sustained period of time the sounds on Brain.fm work a lot better than Spotify. Note that the app requires you to be online so when I’m on a plane or somewhere without access to the internet I'll use the Noisli app. Not as good but gets the job done.

Astro is an AI-powered email application. It's pretty amazing and I'm not sure I'm getting everything out of it that I could. The more you use it the smarter it gets. It does a great job of building a priority inbox based on the emails you open and the people you email often. And it has a bot that pushes questions to you about your contacts and makes recommendations and reminders to follow up on important emails. It also can track email opens and has a send later feature. I understand that there's a lot more coming as Astro is building a big AI company around the app. The sooner you download this one the better. 

The VentureFizz Podcast

I did a podcast with Keith Cline from VentureFizz a few weeks ago. We talked about my career, how I think about growing startups and lots of other stuff. You can listen to it on iTunes here or on Soundcloud below. 

Welcome to Episode 14 of The VentureFizz Podcast, the flagship podcast of Boston's most trusted source for startup and tech jobs, news, and insights! On this episode, VentureFizz Founder Keith Cline is joined Brian Manning, who is the VP & Head of Growth at PatientPing, a healthcare technology company in Boston. He built out successful businesses at Zocdoc and NextJump, and he’s focused on doing the same at PatientPing, a company backed by leading VCs like First Round Capital, Andreessen Horowitz, F-Prime Capital, and others. In our interview, you’ll hear about Brian’s background, his ability to succeed in a role usually handled by multiple people, his thoughts on creating a growth strategy, and lots more. Lastly, if you like the show, please remember to subscribe to and review us on iTunes, or your podcast player of choice! And make sure to follow PatientPing on Twitter @PatientPing and VentureFizz @VentureFizz.

The Attributes Of A Great Strategic Salesperson

Strategy Defining the attributes to look for in any new hire is really challenging.

People are complex and every situation and every environment is different. So it's extremely difficult to apply a blanket set of attributes that will lead to success in any job.

I’ve found that this is particularly difficult with “strategic sales” roles in a startup. By strategic sales I mean a role where a salesperson is selling a highly innovative product into a large organization that requires a large investment of time and/or money from that organization.

It’s important to define strategic sales because the skill set required to be able to close strategic deals is very different from the skill set required to close smaller, more defined, "transactional" deals. Often, success in transactional selling comes down to simple hard work and effort. If you analyze a transactional sales funnel you'll see that there actually isn’t a huge difference between conversions for high performing salespeople and conversions for low performing salespeople (by conversions I mean things like 'phone call to meeting set' and 'meeting held to verbal commitment'). Success in that world often comes down to volume. More calls = more sales.

While there’s certainly nothing wrong with good old-fashioned hard work -- in fact, it's a requirement -- strategic sales is almost exactly the opposite of transactional sales. Conversions really matter and lead qualification is even more crucial because strategic deals require a huge time commitment from the salesperson. And there are massive differences between the conversion rates of high-performing salespeople versus low-performing salespeople. A high-performing strategic salesperson can convert 100% of their meetings into an active sales cycle; a low performing strategic salesperson may convert none. Literally zero. Strategic sales is not a numbers game.

Ben Horowitz likes to say that closing a deal with a large organization is like passing a law in congress. And it’s even harder than that when selling innovation — there's no set process for the buyer to buy within their organization or budget to buy the product. And in a startup, you’re small and nobody knows you and you don’t have a clearly defined sales process and you don't have perfectly polished sales materials. It’s really difficult.

I've thought a lot about the attributes that are most closely correlated with success in strategic sales. I've seen a lot of successful strategic salespeople and a lot of unsuccessful strategic salespeople. It's a problem I've been trying to understand for years.

Recently I’ve spoken to a number of people I trust on this topic and here’s where I think I’ve landed. Here are the four key attributes of a successful strategic salesperson.

Insatiable curiosity

In order to solve a complex problem you need to fully understand it. How does the buyer buy? Who has influence in the organization? What value do customers see in the product? What does the customer do during the day? How is the buyer bonused or promoted? What other options does the buyer have?

I could literally write 100 more questions like this. A strategic salesperson must always be wondering about the answers to these questions. They should constantly be learning from their customers, their leadership, their colleagues, the media, their competitors and anyone else that will talk to them. They need to be obsessing about the problem and trying to build a story and a solution and constantly iterating their approach.

A person that doesn’t have this level of insatiable curiosity simply won’t figure it out. They'll get stuck.

Optimistic grit

I’m fusing two attributes together with this one but I think it’s necessary. Any type of sale will inevitably lead to lots of rejection of the salesperson, the product and the company. This sucks. It’s painful. It’s even worse when selling innovation because there will be prospects that think the idea is crazy and will never work and the buyer has no process or defined way to buy the product. In order to get through this the salesperson must be a winner and must have a winning attitude and know that they can overcome. And they must have the grit and determination to keep getting up after they get knocked down. It may sound cliché but it's true. I've never met a pessimist that was good at strategic sales. There will be an endless number of reasons why it won’t work and the only people I’ve seen that will push through have a high level of optimistic grit.

Extreme humility

I used to joke that there are two types of salespeople:

1.) The type of salesperson that flies home from a bad meeting with a prospect and sits on the plane mentally blaming the product, the marketing team, the legal team, their boss or the prospect that just doesn’t “get it."

2.) The salesperson that sits on the plane thinking: How could I have answered that one question better? What else should I add to the presentation? What should I take out? What’s the context of the person that didn’t like the product? Where are they coming from? Does the product I’m selling threaten some of the people in the room? What went well in that meeting and what didn’t go well in that meeting? Who can help me get better?

The second approach requires an immense, almost unnatural level of humility. It’s human nature to point fingers when things don’t go well. It’s also often perfectly reasonable -- because it might actually may be someone else’s fault! But placing energy into #1 is a losing approach. Obsessing about the things that we can control is the way to win. So much energy can be soaked up by complaining and blaming others. Great strategic salespeople transform the energy that most put into complaining and blaming and point it toward improvement.

Ability to educate and inspire

I’ve written before that people buy with their heart and justify it with their mind. This is why I advocate not showing a lot of numbers in an initial sales presentation — the prospect doesn’t know or trust the salesperson yet and they’re generally not buying for ROI anyway. They’re buying because of the way the product makes them feel.

As a result, when selling innovation it’s crucial that the buyer be on board with the salespersons's mission and buy in to their perspective on both the problem they have and the way that the salespersons's company is going about solving that problem. The sale has to be somewhat fun and interesting and educational and insightful. It can’t be boring. I don’t mean that the salesperson has to personally be super charismatic or an amazing  presenter (though that helps), I mean that they have to be intelligent and interesting and insightful. The buyer has to want to get behind the company and the product -- they have to become a true advocate.

It's a lot of work for a company to buy something. It requires security reviews, legal reviews, budget reviews, consensus building and many other activities. It also creates a lot of risk for the champion. If they're going to go on the line and buy an innovative product they have to be excited and inspired.

Great strategic salespeople continuously inspire, excite and educate their prospects.

Some Thoughts On Non-Competes

It was nice to see the news a few weeks ago that Massachusetts House Speaker Robert DeLeo vowed to put new limits on contracts that prevent employees from working for competitors. "Non-competes" that restrict the free movement of talent from one company to another can do real damage to an individual's livelihood and the economy at large. Many people believe that the reason that the explosion of successful tech companies happened in Silicon Valley is because of California's effective ban on employee non-competes. Allowing talent to flow to the best organizations without friction is good for a local economy.

Unfortunately, over the past several months I've seen lots of startups going in the opposite direction by including aggressive non-compete terms in employee agreements.

Many companies take it a step farther and require 'no-poaching' terms in their vendor contracts and even try to collude with other local startups and agree to not steal one another's employees.

I don't think companies fully understand the damage that's being done with these types of arrangements. Let me explain.

Imagine that you're working for a startup in Buffalo, New York (Buffalo actually has a pretty hot startup community by the way). And imagine that there are another 20 tech companies in Buffalo that, at some point, you could go work for -- you have the talent they need and you'd potentially like working for some of these companies. Then imagine that the startup you currently work for requires you to sign a non-compete as part of your employment contract. Then you learn that your company requires all of their vendors and customers and partners to sign an agreement that precludes them from poaching your company's employees.

As your company grows, the number of other companies that can demand your services around your home has dropped from 20 to, say, 12. Suddenly 40% of the companies that would potentially demand your services now can no longer demand your services. So the demand for your services has decreased 40%. You're now 40% less valuable than you used to be.

At a minimum, a company doing this to their employees is unethical. At its worst, it's illegal (Apple, Google, Intel and Adobe recently paid a $415 million fine for colluding on no-poaching efforts to suppress employee wages).

When a company creates an agreement where another company cannot poach its employees, they are artificially reducing the value of those employees and their ability to make a living.

Again, the spirt of this is understandable. Hiring and training employees is expensive and companies want to fight to keep their best people. But addressing employee churn through contracts is a backwards way of handling the problem.

The better (and harder) way of dealing with the problem is to create an environment where good employees feel valued and are being challenged and are working on difficult problems and are developing professionally and personally and are being compensated fairly. Writing contracts to compensate for shortcomings in these areas is cruel and likely very ineffective in the long term. And it's nice to see that the state of Massachusetts is catching on and pushing for legislation that will protect employees and the local economy.

The best way to keep employees loyal is to act in a way that deserves loyalty.

Productivity Hacks

Productivity.png I've added some productivity hacks over the last several months. Here are 5 that have been working well for me lately:

  1. File, Do, Defer. I've started using the "file, do, defer" system. I look at a task (in Wunderlist, a great to-do list manager) or an email in my inbox and decide if it needs action or not.  If it doesn’t need action I either delegate it or file it. If it does need action and takes less than 3 minutes, I do it. If it will take more than 3 minutes I’ll defer to a time when I have more bandwidth and focus. To keep me focused on the 3 minute rule I’ve begun using the Pomodoro app for Mac that tracks the time I spend on a task.  This isn’t to make me rush through the task it’s to make sure I stay focused on it and get it done quickly and don’t get distracted.
  2. Working Offline. I’ve been doing this for years and can’t recommend it enough. I put my email in offline mode, close Slack and focus on initiating rather than responding.
  3. Virtual Assistant. I’ve hired a virtual assistant for personal tasks. There are lots of great services out there but I use FancyHands which has been great. My virtual assistant does everything for me that I don't want to do -- they have have coordinated my move, found me a couch, helped plan a vacation, changed my cable service, researched health insurance plans and booked a New Year's Eve dinner reservation. I’m constantly scanning my to do list and looking for low-value tasks that I can outsource. It's low cost and a massive time saver.
  4. Soylent. I’ve begun drinking Soylent, a meal replacement drink that supposedly contains every nutrient needed by the human body. It’s fantastic. It allows me to have breakfast on the go and sometimes lunch on the go so I can maintain energy with zero time commitment. It’s incredibly helpful on hectic days.
  5. Make projects seem small. We all have those projects or tasks that need to get done but seem hard and time consuming and stressful and keep getting put off. I read about a productivity trick in the book Getting Things Done to help deal with this problem. The trick is that you think about the thing you need to do that you keep putting off and on the bottom of a piece of paper you write down the outcome that you want with regard to the project  -- e.g. what is success? Then break it up until small tasks and write those as a list on the rest of the page. Going through the process of breaking the project into small tasks makes it seem so much easier and actually gets you somewhat excited to go do it.

Hope some of these are helpful.

5 Questions To Ask Yourself Before Joining A Startup

Startup I had a good conversation the other day with a former colleague who’s considering making a move to very early-stage startup. I shared with him the list of questions I ask myself before I make a commitment to working with a startup and thought I’d share them here as well.

A quick disclaimer: startups are inherently risky and these five questions aren’t designed to help you avoid a high level of risk. That’s not the point. These questions are designed to help ensure that you understand the risk and make you a bit more comfortable that you’re making a good decision.

Here they are:

  1. Do you have confidence in the people, particularly the leadership team? There’s a great quote from Peter Drucker that I can’t seem to find where he points out that, when a company finally succeeds, more often than not, it will find that it will end up selling a different product at a different price to a totally different set of customers than it initially had planned. The point is that the startup doesn’t have to have the perfect idea or the perfect product to be successful. What they have now probably isn’t right. And that’s ok. What’s important is that you’re working with an ultra-talented team that can iterate and execute like crazy. I’ve written before that the most critical traits for people working in startups are grit, humility, curiosity and adaptability. If you find that the team you’re working with has these traits you’re off to a good start.
  2. Has the founder(s) earned the right to know a secret? If what this startup is doing is so valuable, why isn’t someone else doing it? More often than not the reason is that the founder knows something that other people don’t. Or at least knows how to execute in a way that others don’t. It’s important to be able to understand the secret that the startup knows and to understand why they know it and others don't.
  3. Can the investors/board articulate how the business could be massive and why it’s defensible? Prior to making a jump, when possible, it’s important to talk with some of the investors and board members. This is a good way to test their engagement and confidence in the company and alignment with leadership. Really push them on why they invested. Ask them what they think the core of the business will be and what they think will come after the core. If they can’t confidently articulate this in a way that makes sense it’s a clear red flag.
  4. Can you see yourself being truly passionate about the work you'll be doing? Startups are tough. You’re fighting an uphill battle most of the time and there are lots of highs and even more lows (at least at the beginning). If it's easy then it's not valuable. I’ve found that dealing with the pain of working at a startup is a lot easier when I truly believe and care about the mission of the company. If you don't care about the impact you'll have beyond your own personal benefit then you'll find that the tough days are a lot tougher.
  5. What are 3 reasons it could fail? Again, most startups are long shots. And it’s important to be humble enough to know that you can fail. If you can’t articulate 3 reasons that it could fail, then you either don’t understand the business well enough or you aren’t taking the risk very seriously. Do your diligence such that you understand as many risks as possible and the reasons it might not work out. If after truly understanding the risks and potential pitfalls ahead you really feel like you still want to make the move then you've probably found a good fit.

The Consumerization Of Procurement

The other day I was talking to a founder of a B2B software startup about how hard it is for big companies to buy things. Even at a super low price point (a couple hundred bucks a month) software purchases still have to go through a litany of approvals. I was telling her how almost exactly two years ago I wrote a post titled, Individual Employee Budgets, where I predicted that employees would have their own discretionary budgets that could be used to buy things that would make them more productive and profitable employees. With the growing trend towards the consumerization of enterprise and the ability for anyone in their basement to build and distribute a great productivity application to millions of employees, individual budgets, I thought, would be a requirement for companies to succeed and retain employees. For smaller purchases, traditional procurement eventually has to get out of the way.

I still believe this will happen, but it's moving much slower than I predicted.

That said, two years after writing that post, when I think about the software I use to get my job done, much of it is 'consumerized'. That is, it's sold directly to me and in order for me to use it my company doesn't have to go through a painful procurement process. Software like Wunderlist, Google Maps, TripIt, Sunrise, Feedly, Evernote and Google Docs, to name a few. There are only a couple of applications that I use that were procured through a traditional procurement process -- and most of those aren't as useful or as easy to use as those that I procured myself. Self-service software has to be really, really good as the switching costs are near zero.

It's disappointing that the way companies buy hasn't become more flexible as enterprise software has become more consumerized and easy to procure. Employees are ready for self-service productivity tools and software makers are ready to build and distribute them. The only thing we're waiting for is for big buyers to let it happen.

7 Lessons From A Tough Negotiation

Lots of people that know me know that I'm huge fan of Bill Belichick, the coach of the New England Patriots. The thing I like about him more than anything else is that he never, ever makes excuses. When the Patriots lose a close game, the media will ask him about the weather, the referees, the tough schedule, the rules, the player injuries, you name it. And he never acknowledges any of it. He only talks about the things that his team can control. As a result, he's the winningest coach of the last decade. He obsesses about what he can control and ignores everything else. That is the exact approach people should take at work -- especially when negotiating a deal. You can't control the prospect, the prospect's attorneys, the bad economy, your product capabilities, the law, or your executive team. You can only control your own actions. And when you fully take that approach, you'll find that your energy won't go outwards towards things you can't control, but will instead go inwards towards things that you can. That's how you get better. That's how you win.

I recently finished a long, painful and frustrating 3 month negotiation. Thinking back on it, I'm tempted to blame the other side or blame other factors for why it was so long and so frustrating. But that's not helpful because I can't control any of that. I can only control what I do and try to do it better.

So with Bill Belicheck in mind, here are seven tactical things (that I can control) that I'll do better next time:

1. Never assume the deal is done. Make sure you have asked and asked and asked about the other side's approval process. More often than not someone is going to come along to do one final review of your deal. Document their process and track to it.

2. When you've created urgency, continuously validate that the other side values that urgency. Over a long negotiation they may not.

3. In addition to urgency, throughout the negotiation continuously reinforce your value and why the other side should want to partner with you. Don't get too caught up in the weeds and the specifics of the deal and neglect to remind the other side why they wanted to partner in the first place.

4. Have a 'time and energy walk away point'. Most negotiators know the concept of BATNA (best alternative to a negotiated agreement) but don't forget to include your own time and energy in that calculation. Take this really seriously. Focusing on a deal that is too time consuming has an exponentially negative effect. You can dig yourself deeper because you're not focusing on other opportunities and you lose your leverage (you need the deal more now because you have fewer options now because you've been too focused on this one deal).

5. When you're down to the last few items, setup a recurring daily meeting with the other side until it gets done. It's amazing how you can lose weeks if you don't do this. People get busy and each side may use time lags to build leverage.

6. When things get ugly, negotiate in person. Your situation will improve 10x faster in person than it will over the phone.

7. Bring in other people. I tend to be a lone wolf when it comes to these things. It's better to have multiple personalities involved. Two people are harder to read than one and the other person will always think of things you haven't.