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.

Some Advice For People Joining A Tech Startup For The First Time

Joining a tech startup for the first time is extremely difficult. If you’ve come from a big public company or a non-profit or the public sector it can feel really unnatural and even uncomfortable. The way you’ve operated in the past likely won’t work. Things will feel weird.

I’ve had the luxury of working in five different tech startups and have been in a position to see trends around the things successful people do and the things the not so successful people do. Here's some advice based on what I've seen over the years. I hope it’s helpful for people that are joining a tech startup for the first time. 

Be incredibly good at dealing with change. Depending on the number of employees in the startup, headcount can literally double in a month or even a couple of weeks. The number of customers serviced can double. Cash in the bank can grow by 1000x. A crucial employee can quit. A major customer can cancel. Because startups are small, change and its impact can feel radical. The company can become a different company in an instant. This is a strange thing. This doesn't happen in a normal company. In addition, in the early days, a startup is really just a hypothesis about solving a problem. And the way that the company is solving the problem will change constantly. For the employee, this means they are likely to have different bosses and jobs and roles and projects in a short amount of time. Learn to enjoy and thrive in this change. 

In your first 90 days do something awesome. When you join a startup, because of its small size, you’re going to have a lot of eyes on you — particularly from people that can make decisions about your future. Find a way to impress them. Take ownership of a project or a sale or a product or a process improvement and dive in deep and make it great. Be transparent about what worked and what didn’t. You’ll find that failure is generally not frowned upon and learning is highly valued. Doing something awesome is not necessarily easy. It’s not going to come to you. Have zero expectation that someone is going to set you up for success. Go get it and make it happen. 

Avoid playing politics. In larger companies, to get ahead you have to play the political game. This is much less true in startups. In a large successful company an employee can do nothing and play politics and the damage to the company is non-existent. The great employees aren’t playing this game and if you are you’ll stand out. People will pick up on it and you’ll get a reputation as someone that is political and it’ll be hard to shake. Get stuff done and be transparent about your success and learning. The downside of a startup is sometimes if one person doesn’t like you it can hold you back because there isn’t a defined system to move you forward. This is why you should avoid playing politics because it’s a quick way to get people that matter to not like you. The way to be liked is to produce results and share what you're learning.

Think short term and long term. This is one of the hardest things to do. It's not natural but it's necessary. The main thing that is going to get you ahead is your ability to produce short-term results and to be transparent about those results (and your learnings). You have to think short-term and show weekly if not daily progress. But you also want to have a longer-term point of view on your industry and where things are going. Your leadership team is getting paid to predict the future and that's hard to do. They will love the employee that can deliver short-term results but can also act as a thought partner in how the company should be thinking about longer-term strategy.

Make work a very big part of your life. There are times in our lives where we want to focus lots of attention on things outside of work. If you’re going through that time in your life then I’d encourage you not to join a startup. A startup’s cost of capital is generally extremely high. It costs the startup a lot of equity value to raise the capital needed to pay your salary. Because of that, there will be high expectations around your commitment and production. This is a crucial point. It’s simple math. It costs much more for a startup to employ you than it does a big company. And your impact is also greater. If you’re in a 30 person team your contribution, on average, is 1,000 times greater than the same person in a 30,000 person company. The startup is going to rely on you greatly. If you’re uncomfortable with that pressure you’re in the wrong company. 

Be humble. It is enormously difficult to effectively operate in startup if you’re not humble. It almost can’t be done. The way you are doing things today is going to change dramatically because it’s not right. Your product isn’t right. Your pricing isn’t right. Your process isn’t right. Your go-to-market isn't right. You have to have a perpetual curiosity about what can be done better, the humility to recognize it can be done better and the willingness to go out and do it better. If you can’t check your ego and do this well you will fail. 

Hire people that are better than you. When you’re hiring people there’s a temptation to make sure that you’re not hiring someone that can take your job. Do the opposite. Hire people that can take your job. This may not feel natural but I’ve found over and over again that people that are willing to take this approach win because they build A+ teams and that’s much better than the safety that comes from hiring a B team. A+ teams create exponential value. B teams create linear value and in some cases negative value. 

Be insanely commercial. Most startups are not sustainable. If they weren’t taking in outside capital they’d go out of business. Be very aware of this reality. This is not a comfortable situation for the executive team. By definition it’s uncomfortable. Embrace this reality and get onboard with leadership in understanding that it all could come crumbling down. Commercial success is the only thing that matters in the early days.

Challenge yourself to understand context. Because things move so fast and there often isn’t clear ownership and process, decisions made by leadership or other teams may seem dumb. People may seem incompetent. This generally isn’t the case. At one startup I worked in I had the luxury of working closely with the leadership team but I wasn’t on the leadership team. I’d be in the room and see how leadership made decisions and then I’d be out for drinks with my peers and they’d complain about how leadership was clueless and didn't make good decisions. I couldn’t believe what I was hearing. The problem wasn’t that leadership was incompetent, the problem was that my peers lacked the context and lens that leadership was operating under. Challenge yourself to not dismiss seemingly bad decisions as people being uninformed and try to see the decision through the other person’s eyes.

Consider doing the impossible. If you dive into the history of most extremely successful startups they probably did something at some point that seemed impossible. This is true of most major success stories. For some reason, I always think about poker on television. Today, millions of people watch poker on television but there was a time when this was a crazy idea. The reason was that the great players would never agree to have the cameras see their cards during a game. And if the viewer couldn’t see the cards all the drama would be lost. But it was a non-starter with the players. No way. Never going to happen. But some ambitious TV producer saw the opportunity and didn’t accept that reality. He forced it and found a way to get the players to agree and now television poker is a multi-million dollar product. Consider the things that you think are non-starters or are impossible and try to see if you can find a way to break through. Don't be the naysayer. Be the one searching for the solution to the impossible problem. Find a way.

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.

Time

I recently reread Peter Drucker’s The Effective Executive. The entire book is gold and much of it is centered around the way we manage time. This is how he describes time:

"The supply of time is totally inelastic. No matter how high the demand, the supply will not go up. There is no price for it and no marginal utility curve for it. Moreover, time is totally perishable and cannot be stored. Yesterday’s time is gone forever and will never come back. Time is, therefore, always in exceedingly short supply. Time is totally irreplaceable. Within limits we can substitute one resource for another, copper for aluminum, for instance. We can substitute capital for human labor. We can use more knowledge or more brawn. But there is no substitute for time. Everything requires time. It is the one truly universal condition. All work takes place in time and uses up time. Yet most people take for granted this unique, irreplaceable, and necessary resource. Nothing else, perhaps, distinguishes effective executives as much as their tender loving care of time."

Time is a pretty unique thing. I’ve recently started the habit of evaluating how I spend my time by looking back on my calendar every couple of months. When you’re going from meeting to meeting to meeting all day it’s really easy to think you’re spending your time wisely. I’ve found that I’m often not. And doing a frequent look back helps me change that.

The Attributes Of A Great Strategic Salesperson

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

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

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.