Even when things are going well, startup life is hard. Market conditions change, a key customer churns, a competitor shifts their strategy, your app goes down, and so on. As a leader, you're expected to help your team navigate these changes as well as steer the ship in the right course, correcting as you go. Every day it seems there's a new challenge. While many of these will be unique to you, the types of challenges you'll face are predictable and have data‐driven ways of overcoming (how to deal with missing a number, a team member quitting, a customer churning, etc.).

Knowing there are landmines won't help you avoid them entirely, but you can understand how to deal with and contextualize your experiences so you feel less alone. This chapter was one of the hardest to write, not because of lack of material (my network and I have faced many, many setbacks), but because of how endemic failure and struggle is to the startup ecosystem. It's like the water we're swimming in, so woven into how we build and grow new companies to the degree that it's almost, ironically, less visible. This, I believe, is one of the most crucial topics to address if we want to increase diversity and inclusion in the startup ecosystem. Many startup leaders internalize a narrative that everyone around me can navigate this volatility and failure, so how come I'm struggling?

The narrative goes like this: “This was supposed to be hard, but I'm having an especially hard time, so there must be something wrong with me as a leader and maybe I don't belong in the startup world.”

Over‐personalization of a systemic issue (startups are hard, failure happens, no one can be good at everything or anticipate everything every time) hurts everyone, but especially members of under‐represented groups. Many of us have internalized that we need to be better than average (read: the straight white male majority) and to perform at a higher level, because many expect us not to succeed (even if this is unconscious), reinforcing racism, homophobia, transphobia, and other forms of systemic biases.

Who gets to “pick themselves up again” and get second and third and fourth chances after setbacks is highly related to systemic oppression. Straight cis white males I interviewed for this book had very warm and glowing things to say about times when they failed and someone “brought them back into the fold,” offering them another chance, a new opportunity, or an even better job because they proved they learned from the past setbacks.

The warmth and kindness from others who'd been in the same situation allowed them to de‐personalize their failures because other people did. Egregiously few women and minorities make it to the leadership level, and we see drop‐offs at the seniority level for those who have made it. Studies show women over thirty‐five, for example, drop out of the startup world at twice the rate as men.¹

When we normalize difficulty and setbacks for everyone and give everyone a fair shot to try again (at least at another startup), we help the entire ecosystem. We will all experience failure if we work in startups for long enough. All of us, at some point. If you're a member of an under‐represented group, and you fail, you deserve to continue on your path. The toxic perfectionism double‐standard must not continue if we want to see more under‐represented people in startup leadership. When we normalize and de‐personalize the painful yet common experience of startup failures, we can see that this is part of the process and not a “problem.”

If you want to be in the startup world you deserve to be here, learn and grow. This is that warm message from the universe telling you that you are so, so worthy of being here if you want to be here. You can grow from failure too, no matter your identity. Ready to dive in? Let's do this together.

LEARN TO PRACTICE COMPASSION TOWARDS YOURSELF WHEN DIFFICULTY AND FAILURE HAPPEN (BECAUSE THEY WILL)

We're all going to hit the rocks at some point on our startup voyage. All of us will underperform or face difficulty if we're in the startup world long enough. When a person who is a member of an unrepresented group doesn't know something or underperforms in some way at a startup, it's hard to explain the weight of “it's because you were never meant to be here” (both from external and internal sources) to explain to peers in the majority. Dominant culture doesn't feature us in the roles based on the small percentages of us in the industry, so when we mess up, it can confirm that bias, rather than seeing mistakes for what they are: common mistakes.

In her book Fierce Self‐Compassion: How Women Can Speak Up, Claim Their Power and Thrive, Dr. Kristen Neff shares that we have to be able to extend the same care towards ourselves as we do to a good friend.

“[In addition to kindness] we also need to be able to see our flaws, admit our failures, and put our own experiences into perspective,” says Neff.²

There are areas you may have to improve to stay in your job (if you want to) or create an empowering narrative of growth and learning at your next opportunity. You can work on the areas that are being called out for competence issues without making it “true” that your competence isn't valid—at least until you find a place where it's safe to learn and make mistakes without questioning your competence or abilities as an executive.

PRACTICE SELF‐COMPASSION WHEN THINGS ARE HARD AT WORK

We are human and it's normal to feel challenged when we struggle at work. We can bring compassion to the experience, acknowledging it's hard while reminding ourselves that there are other resources out there and it's okay to get help and support in forms like exercise, meditation, yoga, therapy, coaching, and talking to friends and loved ones.

“When we recognize we've made a mistake, self‐kindness means that we're understanding and accepting, encouraging ourselves to do better next time … we stop to say ‘This is really difficult. How can I care for myself at this moment?’ ” says Neff.³

UNDERSTAND THAT PEOPLE REACT DIFFERENTLY UNDER STRESS

Under stress, people act differently due to how human bodies are wired for survival. We have less rational, reptilian brains that are triggered into fight–flight–freeze–appease reactions. These behaviors are coping mechanisms that we evolved to help us survive. If someone is acting out of character and/or disrespectfully (including you), you can guess it's probably due to a stress reaction. This doesn't excuse any bad behavior, but it can help you depersonalize it and address the behavior while continuing to hold space for the person.

At startups (and everywhere), people's norms differ for what respectful behavior looks like. At startups, power dynamics also influence who gets to act out their stress in unhealthy vs. healthy ways. A CEO is more likely to have carte blanche with few consequences to unload stress on others than a lower‐tier employee. How we all deal with our stress reactions matters a great deal to create an empowered, healthy work environment.

Examples of healthy ways to deal with stress include going for a run, doing yoga, talking to a therapist or coach, or taking a break from work to resource oneself. An example of an unhealthy way is to yell at colleagues when you're anxious or angry. Avoid the latter, and you'll be light‐years ahead of most people in the startup world (unfortunately).

TREAT PEOPLE WITH RESPECT, ALWAYS

Startup leader Matt Harada goes out of his way to be kind, even (especially) when he is under stress. He values the people and relationships enough to be kind, even to those who aren't performing in a role (or sometimes are performing but their services are no longer required). He knows his limits and does his own internal work to stay calm under stressful circumstances and not project his emotions on to those around him. He can do this even when someone else is upset.

Harada has taken people out to lunch and kept great communication with folks he's let go. That's because whether or not the business relationships worked out, he still valued the personal relationships. I encourage you to be like Harada and be kind to those even as they're on their way out the door (even as you're the one showing them out). Put your energies towards regulating your own emotions so you don't expect others to absorb your stress. If you make a mistake in this arena, apologize and own up to your behavior and take steps to guarantee it doesn't continue.

WHAT TO DO IF A COLLEAGUE QUESTIONS YOUR IMPACT

The “eye of Sauron” refers to the intense scrutiny that can move from one department to another, common in the startup world. Eventually, it will come to you and your department, and your ability to deliver results will come into question. This doesn't necessarily mean that you aren't valued as a leader; it's common and it rotates around startup teams to give other teams visibility and resolve issues in departments.

The hyper‐focus on your area is jolting the first time you experience it. It can come from your CEO or a peer, a cross‐functional partner, like the Sales leader if you're in Marketing or the Finance leader if you're in Sales, etc. This can bring up a lot of feelings, especially if the delivery (context) isn't handled in a kind way.

For people from under‐represented backgrounds, someone calling out our inexperience in an area we “should” know, missing a number, or being treated like “lesser than” other executives can be especially painful. It's known in Buddhism as a “double arrow” to suffer twice; the first arrow is the mistake being made and how that impacts you and the second is the additional suffering heaped on top of it by shaming ourselves or feeling bad.

Multiple times in my career, I have made a mistake comparable to or lesser than a straight white male peer of similar background and experience level. When he made the mistake, he was disciplined or had it pointed out in a neutral way (no consequences). When I made the mistake, it called into question whether I deserved to be in the role. Being a member of an under‐represented group can mean we are constantly questioned for our credibility, and even the slightest mistake or lapse (or a big lapse) can prove “we weren't qualified to be here after all.”

Surprisingly few people are good at giving feedback directly. Occasionally, a disgruntled colleague worried about their own success will express concerns that they feel are tied to their program and the business's success.

Some strategies for navigating negative feedback from a peer, particularly if it's not delivered to you directly:

• Attend to your feelings. Practice Neff's self‐compassion affirmations. Get support in the form of an outside party like a coach or a therapist. Let yourself feel whatever is coming up for you, and process with an expert how this might relate to past experiences. Go for a run and eat healthy food and try some yoga and meditation. Cry, process it alone and with people outside of the company whom you trust, and try to get yourself out of an elevated or flooded emotional state where your higher‐functioning brain is hijacked and back to a calmer state where you can proceed to make decisions.
• Address the content of any concern with your colleague and/or CEO. Once you're calmer, discuss the performance issues directly. If there are issues to resolve, talk about how you're going to resolve them (e.g., a failing area of your function may need scaling up, and here's your plan for doing that).
• Address the context of the issue. If information was conveyed in a way that made you feel disrespected, you need to build that working trust and address the “how” in the communication that didn't work for you and made you potentially feel bad, or even psychologically unsafe. Talk about how the context is impacting you and what your needs are.
• Get additional data if you need to. If you're unsure whether you're “seeing the same game” and understanding the issue you're being called out for, dig into the data and concerns so you can work together to discuss the solutions your team will implement.
• Make requests to get your needs addressed. Make a request to this colleague that is questioning your abilities to, say, go directly to you with feedback in the future rather than the CEO. Ask the CEO to call you with feedback vs. slacking you on the weekend, etc. If you ask for what you need, there's a higher likelihood it'll be met.
• Make your colleague and/or CEO a part of the solution. Make a plan, based on the data and those conversations, to fix the underperforming programs and predictably raise the numbers to hit our goals.
• Socialize that plan with this colleague directly, first. Model the way you want the relationship to be.
• Share that plan with the CEO and cross‐functionally, and/or to the rest of the company. Ensure everyone understands how you're addressing the issue. Communicate the results to the leadership team and to the company, if appropriate, so everyone understands the changes made, how everyone on the team is contributing, and the impact that these efforts had on improving numbers and driving results.
• Crush those numbers. In the end, a colleague or your CEO raising concern about your program can help the company excel.
• Do a retrospective. After the content has been resolved, it's important to address context (earlier, if possible). What went well with the feedback process and what needed improvement? Were there any areas where you need to re‐establish trust or build a better working relationship? How can you partner better in the future to prevent this challenge from reoccurring?

Getting constructive or negative feedback doesn't have to signal the end of your time at a company. Particularly if a colleague has gone to your boss or CEO to give this feedback without telling you first, it can be painful. In the psychology world, this is often referred to as “triangulation.” While direct feedback is healthier on teams, this is surprisingly common behavior. It can be easy to sink into shame, particularly if you feel like you've been “tattled on” for some reason or that you're being questioned as to whether or not you're a true leader in your area. This often comes up in famously embattled departments like Customer Success and Sales or Sales and Marketing.

Learn from any improvement opportunities, but don't let it tell you anything about your worth in the startup world or whether you belong there. Don't let anyone else control your destiny in the startup world. At the end of the day, this is a job. There will be more jobs if this one doesn't work out.

IF YOU FAIL AND GET LET GO, OR MESS UP IN A BIG WAY, YOU STILL BELONG IN THE STARTUP WORLD AND YOU'RE GOING TO BE OK

You may fail at a leadership job, especially your first leadership job, despite trying hard and doing all the things as best as you can. It doesn't mean you weren't meant to be a startup leader. It doesn't mean you're never going to be qualified. It doesn't actually have to mean anything about the future. It means you didn't get it right this time and didn't fix it in time and so you had to go in this particular instance. You can try again, and learn from it. You are still worthy of being here.

I speak from experience when I say I've definitely felt the burning behind my cheeks when I flubbed a presentation or didn't execute something well. “I shouldn't be here,” is the thought that many of us can have. Please be kind to yourself when this happens. Those thoughts can come and go, and it doesn't mean you don't belong.

WHEN YOU GET PASSED OVER FOR A PROMOTION OR A ROLE

I recently caught up with an executive candidate whom my organization didn't hire at the time. She reached out to schedule a time to chat, and I was happy to. I didn't know her well prior to her candidacy with us and didn't have any other special relationship with her, so I was surprised that she wanted to connect.

This woman is a well‐regarded leader in tech, highly experienced in her areas of expertise, and she told me she's loving her new role at a well‐funded, respected, successful company. I listened, congratulated her, and we talked about our families and current events. But then all she wanted to talk about was … why we hadn't hired her a year ago.

She wanted to know why, what she did, and what the “real” reason was. She played the hiring decision back to me as she saw it, repeating interview outcomes and things people said. I had to jog my memory but this was all so fresh in her mind that it was like only the other day.

I was struck by her exasperation, more than a year later, regarding the decision not to give her the role. I was not the decision‐maker on this hire, which she knew. After some more venting, I set a boundary and suggested that she ought to go directly to the hiring team with any questions or additional feedback.

I softened when I realized she was taking this decision very personally. I knew it wasn't personal. I knew some of the dysfunction behind the scenes. I knew that there were political reasons why someone internally was likely going to be promoted vs. bringing in someone new. I couldn't tell her any of this, it wasn't my place, but what I did tell her, this badass woman who was crushing it in her new role was this: she deserved to feel seen. She deserved to be in a role and at an organization that recognized her talents and experience, and that was excited and ready to bring her aboard to make an impact. I said I had no doubt that she would be making a very big impact in her new role and that I was excited to watch her journey.

As someone who has both not gotten jobs I've gone out for and as someone who hasn't offered candidates jobs, I know it's never easy on either side. Like in business and in relationships, it's about mutual fit. If someone or a startup doesn't feel you're the right fit, it says something about them and their needs, and not about your inherent worthiness. Try not to hold on to arbitrary decisions years later. Now go forth and find that fit (if you want!)

NORMALIZING SET‐BACKS AND GIVING YOURSELF PERMISSION TO FAIL AND LEARN

Taylor McLemore, who runs Techstars Workforce Development Accelerator, says he's experienced generosity and chances to start anew after setbacks and failure. He knows this isn't necessarily something members of under‐represented groups will receive.

McLemore says he once failed in a big way and felt “paralyzed.” He says he sent a letter to investors, supporters, and other team members on what happened.

“I was in a very sad, dark place when I sent that letter. It was the end of something that I really believed in and cared about as a company,” says McLemore.

He says the rest of the emails surprised him: they were supportive. People offered him jobs and offered to connect him with their networks, especially those who had been in his shoes before and could empathize (and see themselves in him).

McLeMore said he wished we could extend this generosity around failure to everyone in the startup ecosystem. (He is a self‐identified straight white cis male.)

IS IT TIME TO CALL IT QUITS? NO ONE GETS TO DECIDE WHEN YOU STOP BEING A STARTUP LEADER BUT YOU

There are many great reasons not to work in startups, and no one but you knows what you need to protect your health or manage other priorities. If you want to quit the startup world, you are free to do so. The startup world can be a rollercoaster and there's no harm or shame in quitting.

I implore you: if you do want to stay, if the only thing keeping you from staying is a setback at a particular job, please know that you deserve to be here and should be here if you want to be. There are other companies with different CEOs, different founders, different customers, and different products. Don't let this one configuration or setback dissuade you from working in startups.

REFRAMING FAILURE AS ANOTHER LEARNING OPPORTUNITY

Executive Erin Rand, says there are two options: success or learning.

“Failure, really, is then an illusion,” says Rand. We've all had this experience and you will too if you stay in the startup world.

Remember that no one but you gets to have the final word on:

• Whether or not you're “cut out to be” a startup leader. The truth is, no one is cut out to be an executive. It's a thing we made up as a society and the criteria change just as companies change and disrupt the tech landscape. If you want to be a startup leader, even if you're not “there yet,” you can work on areas that are worth improving. But there's no “cut out,” and certainly not that someone else could decide for you.
• Whether you're “data‐driven” or “analytical” enough. If you struggle with being data‐driven, a common issue for scaling executives, you can take online courses (many of which are free), read Cole Knafflic's book on Data Visualization for Business Professionals (highly recommended), hire a coach or consultant (sometimes your company will pay for this), and find other ways to learn how to become more comfortable with data.
• Whether you're a good manager or leader. Okay, this one can feel really bad, especially if you mess up something with a direct report. But like startup leadership, a concept made up by humans, being a good manager or leader is a skill we have evolved and can learn. If you've muddled something, you can learn from it and do it better next time.
• Whether you have enough “gravitas” as a public speaker. I've had plenty of people warn me I'm too shy to be a startup leader. If I'd listened to them, I'd never have experienced the joys of a flood of messages congratulating me after moderating a panel in a packed room of 1,000 people (back when we used to pack rooms in real life) at a Techstars Demo Day or speaking in front of hundreds at Lesbians Who Tech. I hired a public speaking coach. You can overcome any public speaking concerns if you want to with Toastmasters, Improv, and coaching.
• Whether you're “scalable” as a leader (up or down in company maturity/size). Again, there are real things to work on here to be successful in the level of execution and strategy you need to rock it at a startup leadership role. But don't let someone tell you definitively you're not scalable. If someone says “you'll never be a startup person, that's not who you are” or “you'll never scale up to grow a bigger organization” that may be true at that moment (or not!) but that's absolutely something you can work on if you want. If you choose to stay in a particular area of the startup world based on size and maturity that you're excited about, great. But don't let someone else tell you that.
• Whether you're good enough at your function to lead it. This may be something we all hear at some point, if only in our own heads, but remember to tell that voice that you can always improve and anything you don't know you can learn or hire around.
• Whether you belong in the startup world! If you want to lead at a startup, and you work hard, you deserve to be there. Period. There is no gender, sexual orientation, ethnicity, ability, age, or another external marker that determines worthiness. Just because you don't see people who look like you in the roles (yet), doesn't mean you don't belong.

It is possible that a job will end abruptly, either because of you or your employer. That doesn't mean anything has to be said and done for you and your leadership career. If you want to be a startup leader, and there's a real area to work on, you can work on it. You can try again. If you choose not to pursue a startup leadership career because it's not right for you, and you're happiest in other roles, fantastic. Go for it. But don't let someone else close the book when you're merely at the end of the chapter.

OTHER TYPES OF SETBACKS

OTHER THINGS THAT CAN GO WRONG AND HOW TO DEAL WITH THEM

ADVERSITY IN THE STARTUP WORLD IS A FEATURE, NOT A BUG

According to Mike Tyson, “everybody enters the ring with a plan and a strategy and then they get punched in the face.”

At some point, all startups will hit bumps in the road. A CTO will quit. A lead investor gets fired from their firm, and the new investor is no longer a champion. Lead customers churn. This is startup life.

“It's not easy,” says Jeff Bussgang. “I had a note from one of my partners that one of our founders is tired and is just having a hard time pushing forward. We're all very thoughtful and sensitive about mental health and illness and energy depletion, but when entrepreneurs are tired, it's over, it's done. And so they've really got to rally themselves to keep that energy level high, then rally their teams,” says Bussgang.

NAVIGATING PIVOTS SUCCESSFULLY AS A STARTUP LEADER

Along the way to “up and to the right” growth, there may be a significant change in direction, otherwise known as a pivot. The way to get through? Lots of communication.

Before their pivot, entrepreneur Hiten Shah's company raised money from investors for what they were working on prior to the pivot.

“We continued sending our regular investor updates, which were a monthly first Monday of every month at 8 a.m. investor update. No matter what period, they got sent. It's just in something (my co‐founder) Marie and I both worked on that has my name on it, but we both worked on it and got it done and it's our investor update for our investors to let them know what happened that month so that they're in the know if we weren't doing that. The investors would not be on board with the pivot if we weren't doing that,” says Shah.

Shah says he and his leadership team were transparent in sharing these pivot updates with everyone at the company, from the interns to the investors.

TREAT PIVOTS AS A CHANCE TO BECOME A BETTER COMPANY

Shah says they pivoted in a way that enabled the whole company and investors to have full transparency because this was the approach they knew would enable them to win.

In a pivot, as an executive, you may not have all of the information that founders and co‐founders have. Take it upon yourself to find out as much as you can, share what you can with your team, and help everyone get on board with the new plan.

IN TIMES OF CRISIS, UNDERSTAND YOUR CIRCLE OF CONTROL

We all have things within our circle of influence and control and things outside of it. The “serenity prayer” in the recovery world (Grant me the serenity to accept the things I cannot change, courage to change the things I can, and wisdom to know the difference) applies well to startup leadership.

Shah says people get caught up in territory that isn't their problem or that they can even influence, and they get caught up because they're trying to control things.

“I see a lot of people driving themselves nuts, trying to control things. They don't have control in the work environment and are trying to get upset about all these things. At the end of the day, you don't control it. So then you have a decision to make. Do I stay here? Or do I not? Because that's the ultimate decision,” says Shah.

According to Bussgang, “Nothing fixes morale like winning,” says Bussgang. Get your team in a position to win again with areas you can control.

STAY AND ACCEPT, TRY TO CHANGE THINGS, OR LEAVE?

Shah says when someone complains to him about their job, when it's related to something they don't control, he asks them to reflect on “Are you willing to have patience here and see how it plays out? Or do you want to leave the job? Because that's not in your control.”

In startups, boundaries and roles are blurred and people can impact change across an organization. The key is to consistently ask yourself in a situation if you can control it or if you can influence it.

IN TIMES OF MAJOR CHANGE, CONSIDER HAVING AN “ON THE BUS OR OFF THE BUS” CONVERSATION WITH YOUR TEAM

Executive coach Gerry Valentine talks about “on the bus or off the bus” conversations he's had with startup leaders at key moments of growth and/or pivots when it's clear that not everyone will be “coming on the bus” for the next step of the journey.

“On the bus/off the bus” conversations can re‐establish company morale and that people who are not on board are moving on with the most grace possible.

Valentine says, if possible, companies can give their leaders the opportunity to make it easy to exit the business with a severance package and “part as friends” if people aren't on board with the new vision. The people who stay will be rewarded with a better work environment.

“People could easily have walked out the door and found another job. If people wanted to do that, we would wish you luck and we're doing everything we can for you. But if you want to be on the bus, you're on the bus and we're going to be as clear as we possibly can for you about what we believe that road is going to look like,” says Valentine.

During pivots and difficult times, you need to have some version of that “on the bus” conversation. Startups change, and people and leaders who worked well won't either want or be able to scale immediately. Be really clear and to make it okay for people to say, “you know what, I am not on the bus” and do your best to help them transition gracefully.

IF YOU STAY, KNOW YOU WON'T AGREE WITH ALL DECISIONS

“Don't take decisions personally that are made in the context of where the business needs to go,” says AQUAOSO founder and CEO Chris Peacock.

“If the thing you were working on gets fully sidelined or if the company changes, it's not a personal thing. It's very much more about what the company needs to do in order to probably stay alive. There's a lot of experimentation that takes place and hard decisions have to be made sometimes,” says Peacock.

TURNING A STARTUP PIVOT INTO A STARTUP LEADERSHIP ADVANCEMENT OPPORTUNITY: MINDY LAUCK, CEO OF BROADLY

Mindy Lauck, CEO of Broadly says: “I was at a large company for a long time and a mentor of mine left and convinced me to join a startup with him. So I was excited to go back into startups,” says Lauck. “I joined the team to completely reimagine and rethink the product experience. So it was a pretty major shift. We changed everything, going from a free product to a paid subscription. It really was a different entity by the time the product that the founder had created was produced and it had worked like that for many years. It was a true pivot.”

Lauck was in charge of the strategy, but the product ended up driving the whole company. Lauck identified that the product strategy in the company strategy “weren't so far apart.”

The next thing she knew, Lauck was in all of the board meetings because the product was the focus, and it had started gaining in revenue and market share.

“I was running the board meetings eventually, because that's where the focus was,” says Lauck. “There was one moment in a board meeting, where I was the CEO. The co‐founder kicked off the board meeting and probably spoke for about two minutes and then the rest of the meeting was mine. We didn't actually speak about it at that moment, but things started to feel different,” says Lauck.

During the pivot, when Lauck stepped up to lead the company in a new direction, she was made CEO. She credits her ability to be adaptable and provide value during the pivot as crucial to her leveling up to CEO. If your business is going through a pivot, you may have an opportunity to expand your role or provide additional value along the way.

DON'T TRIANGULATE: IDENTIFY “YOU TWO” PROBLEMS

To the degree possible, let your team work conflicts out together rather than being a go‐between. When a vision or mission is unclear, or goals need to be realigned, you can jump in, but if you're constantly interfering in interpersonal relationships, that causes your team to expect you to do that.

If you or someone on your team is talking about a third party in the company who is not in the room at the time, if you can, bring them in the room and encourage the two people to talk. As a leader, managing people, you can help establish this practice. When Hiten Shah finds himself recommending something like: “Say, I'm happy to facilitate if you want, but this is a ‘you two’ problem. This is not a ‘me’ problem, right?” In many cases, a timely, direct conversation will be the most efficient solution and save everyone from unnecessary go‐between drama.

ON THE FAME/BLAME CYCLE—WHEN THE HIGHS ARE HIGH AND THE LOWS ARE LOW

There is a Buddhist principle about the cycle of “blame/fame,” meaning that we experience both as temporary states. Getting caught up in either can cause suffering. While we often talk about the highs and lows in the context of entrepreneurship, we don't frequently discuss it in the context of startup employees. We absolutely feel the rollercoaster of startup life. Know that the lows are part of the journey and normalize them with your team.

DEPARTURES: WHEN IT'S TIME TO MOVE ON FROM YOUR ROLE

In The Alliance, authors Reid Hoffman, Ben Casnocha, and Chris Yeh frame jobs as “tours of duty.” Today, few jobs are meant to last forever (or through retirement, at least) and one day you'll need to be prepared for when it's time for your startup leadership role to end—either by your choice or the company's.

When it's you making the decision to move on, you'll need to manage the process differently than when you were a manager or even a director. There are different expectations about timing, including how to ensure that the transition of leadership goes smoothly. When you were an individual contributor, you could leave with the confidence that it was “someone else's problem,” whereas as an executive, you're generally expected to be more involved in the transition process.

DECIDING WHEN IT'S TIME TO MOVE ON

The decision when to leave a role is hard. You've put time and energy into being successful. Likely, you've got unvested equity. You may still believe in the mission. Or, perhaps you don't and you no longer believe in the company direction.

QUESTIONS YOU CAN ASK WHEN DECIDING WHETHER TO LEAVE YOUR EXECUTIVE ROLE

• Do you need to change something, and if that thing could change, would you want to stay?
• Do you just need a break or a holiday?
• Is there something fundamental going on where it's not the right match anymore?
• Do you no longer feel aligned with the company mission or direction?
• Is there another role or opportunity that's more aligned with your goals or mission at this stage?

If you do feel it's time to move on based on these answers, and you're ready, here's your plan.

HOW TO LEAVE A ROLE LIKE AN EXECUTIVE

First things first: Forget everything you know about the famed “giving two weeks’ notice”.

“Giving two weeks would be horrifically unprofessional at an executive level when you have that level of responsibility,” says startup executive Erin Rand. “At the VP level, I can't even imagine someone coming in on a Monday and saying ‘I'm out of here next Friday.’ ”

If not two weeks, what's the standard as a startup leader? Typically, thirty days is the minimum amount. In some cases, you might offer to extend that on your way out, depending on your ability and willingness to do so. You might stay to finish a critical project or to cover while the company replaces you since startups don't have a bench of talent that a larger company does. People already have a lot on their plates, so your leaving will make an outsize impact. Plus, there are considerations like ensuring your team is set up for success, the critical projects are transitioned, and you're leaving the company in a good place. Usually, if you're headed to a new place, they'll willingly wait for you.

“I recently hired a new general counsel, and we waited the other side of three months for her because in her previous role, there were major projects, initiatives, and things to finish up. They were in the middle of an acquisition. We were willing to wait for her,” says Rand.

HOW TO GIVE NOTICE

This will depend on the relationship you have with your CEO and/or the person to whom you report. If you're very close, you may have even discussed what a potential departure could look like. While it may be tempting to storm off or depart with a trail of trash can emojis in a Slack thread, leaving with the least drama possible is the best approach, in most cases.

“At a former company, my CEO and I had an agreement that if one of us didn't think it was working out anymore, we would promise to tell each other and create a great plan for the departure,” says Rand. “When I finally did give that notice, I just had to tell him ‘the day has come' .”

If you haven't set the stage for a departure, that's okay, it's not the only approach. You'll need to have a conversation with your manager. Tell them you're planning on leaving, when you'll be available until, and start the process of creating communication, transition, succession, and other “off‐boarding” tasks. It is common for people to immediately follow up with this meeting with a written notice outlining the key facts via email.

WHEN YOU GIVE NOTICE: BE PREPARED TO BE ASKED TO CLOSE YOUR LAPTOP ON THE SPOT

When you give your notice, you may offer a thirty‐ or sixty‐day transition period. You're ready to roll up your sleeves and prepare to leave smoothly, and then … your CEO tells you to close your laptop after the meeting or call. You're done. This may sound harsh but you should be prepared for that scenario. It does happen, so it's worth mentioning. If you can't afford to be out that day for any reason, you may need to plan when you choose to give notice. Some startups are afraid of people stealing Intellectual Property (IP), the impact someone leaving who's still around could have on morale, a personal grievance, and so on, so they want to “walk them out” right away.

The best advice here is to look at how other executive departures have gone at your startup. Does the CEO blow up and force them out the moment they give word? Alternatively, does the company typically work with the departing leader to create an action plan that allows for flexibility around timing and a joint understanding that the transition will be a gradual and mutual one? You'll have a sense also for how firings go: are people let go immediately that day or do they get a bit of breathing room to wind down projects? Often, companies put severance language in hiring contracts, so this is another area to read closely in your offer.

A WORD OF ADVICE: RESPECT THE COMPANY'S INTELLECTUAL PROPERTY (IP) AND DON'T TAKE IT UPON DEPARTURE

This is a strange piece of advice, but here it is: don't take company files after you decide to leave. That looks bad, even if you don't plan to use them and you intend to put them in an ice vault forever and never look at them. (I assume this is where mediocre slide presentations go once they pass on to the next life, but I digress.) Your “why” doesn't matter. You don't want to create any situation upon leaving that could be construed negatively or harm the company. In the event of any kind of legal situation down the line, if you end up getting a role at a competitor (even years later), you don't want that kind of liability. It's not worth it. Be respectful of the company's IP, and know that the lessons and knowledge you've gained will stay with you forever.

ANOTHER WORD OF ADVICE: BE CAREFUL ABOUT POACHING EMPLOYEES (AT LEAST RIGHT AWAY)

Many companies include contracts about poaching employees. Check your contract and be sure to honor it. This mostly applies to taking entire departments (think siphoning an entire sales team from the current company and plugging them in at your new company), but you need to check your legal terms and be careful. There are many schools of thought on this topic, and you'll find conflicting advice, but in my perspective, this is a very long game (hopefully) and people will remember how you treated their company upon leaving. If you take the star employees with you, they're not going to take it lightly, so know you're going to potentially burn bridges.

EXERCISING YOUR VESTED EQUITY AROUND YOUR DEPARTURE

Any unvested equity generally goes away (poof!) when you leave a company. Sorry. But the vested equity options you haven't yet exercised (if you have them) present a choice: do you exercise your shares? You will only be able to do so within the window—usually a highly limited period after you leave—so check your equity terms and consult a lawyer. Sometimes, you can negotiate an extension on your equity vesting period, so if you're concerned about being able to come up with enough cash to buy your equity, it's worth discussing with a lawyer or a tax advisor and then seeing if that could be discussed with your founders.

TAKING TIME OFF IN BETWEEN JOBS

Startup leadership is enervating, and you'll benefit from taking time off (at least a few weeks, more if you can financially accommodate it) between roles to recharge, re‐set, and explore life outside of the office. “I've never seen anyone regret taking time off in between roles,” says startup executive Erin Rand.

Many executives take time off between roles, so if you are financially able and decide to do this, know that it's not something future hiring committees would likely ding you on (if that's a potential concern). Many executives decide to leave their current roles not because they're “running” from their current jobs, but because they have a new exciting opportunity lined up. In that case, you likely have a new job offer and will need to balance the departure process at your current company with your new role's timing.

MAKE A COMMUNICATION PLAN

When people join startups, there's a sense of camaraderie and alignment around a disruptive mission. When a key person leaves, messaging becomes more critical than ever. It's important to be a part of the story of why you're leaving or others at the company will be negatively impacted.

You need to figure out with your CEO how you're going to deliver the news, and what the plans will be for helping your team and other cross‐functional partners manage the transition.

KEEP IT POSITIVE

“Tell the positive story, and there has to be truth in it,” says Rand. “Sometimes you're leaving because you're burnt out, sometimes you're leaving because you don't believe in the mission anymore. For gosh sake, don't leave a void and say nothing, because people will fill in the blanks in the story and it will often not be a good one, because people will have anxiety whenever a leader is leaving,” says Rand.

“You can't leave gracefully while assigning blame,” says Rand.

If you've truly decided the company can't keep you, talking about what's wrong won't solve anything. After all, you're not going to change things, you're out the door, and the company is unlikely to make those changes because you said them as you left. That being said, if there are valuable insights you can provide on your way out the door that show you're still invested in the company's success, feel free to provide them. If you make sure big things don't fall off the table, that's great. Don't make it an excuse to dump on the company on your way out. After all, every startup has its flaws, and the things you didn't want to work through or deal with anymore will become someone else's challenges soon.

BEWARE THE “DILBERT PRINCIPLE” AND LEAVE WITH GRACE ANYWAY

Erin Rand describes what she and her (also a techie) husband Ray call the “Dilbert Principle”: when you leave a company, for the next six months, everything that goes wrong is going to be your fault.

“It's the easiest thing in the world to just put that on the shoulders of whoever's not in the room anymore. It's not personal, and I don't think people do it intentionally,” says Rand.

While you can't control this phenomenon after you leave, do your best to leave as gracefully as possible.