As a startup leadership coach, I get privileged and mostly unfiltered access to the fears, joys, insecurities and dreams of startup leaders. And I’ve started to wonder: what might happen if startup employees understood more about what I know of the emotional and interpersonal struggles their leaders face?

My intention in assembling the list below is to help bridge the empathy gap I often see emerge between startup founder-executives and their teammates, particularly their direct reports.

While I expect these struggles will resonate with many founders and startup leaders, I also anticipate that most leaders (if not all) would never share these out loud for fear of coming across as weak or incompetent.

To be clear: not all these things will be true for every startup leader. It would not be effective empathy to assume that as a starting point. Rather, I’d encourage you to use this list to expand your awareness of what might (really) be going on.

So, the next time your startup executive cancels an important meeting with you (#3) or is surprised to hear about the team’s reaction to a single comment (#4) or otherwise exhibits a behavior you find mystifying or even frustrating, perhaps you’ll think twice before judging or dismissing it. Perhaps instead, you’ll consider some empathy and give your executive a little grace, some benefit of the doubt, or another chance.

Empathy begins with understanding. Here are six things that might be useful to understand about the founders and executives with whom you work:


1) They really can’t give you more headcount and it’s demotivating to hear that request a lot.

We all understand intellectually that startups are “resource-constrained,” but only startup executives live that reality in the fullest sense. They’re the ones looking at budgets; understanding the full cost of adding someone (hint = it’s more than just their salary); counting down months of runway, and denying requests for adding headcount on a weekly basis.

It’s an intoxicatingly easy solution to ask for headcount (and of course, sometimes it is the right one) but more often than not it’s just not a viable one—and it’s rarely the only one.


How to Act with Empathy:

  • Be the (rare) teammate who understands these tradeoffs, and doesn’t take a singular perspective in advocating for more headcount.
  • As much as humanly possible, be realistically creative about how to do more with fewer people.
  • Propose everything else first before turning to headcount as the last-but-necessary alternative.


2) Their investors are (usually) a huge distraction and (sometimes) an emotional energy sinkhole.

Many startup employees respect their founders for raising money over and over again. They appreciate how their leaders seem to magically court investors and woo the board. But respect and appreciation are different from empathy. Being in awe of your founder for how well s/he courts investors is different from really getting it—from really understanding the emotional toll investor relations can exact.

There’s a reason you probably don’t have full understanding here. Most founders, when they’re undergoing investor-induced stress, will not let their teammates know. They assume their role is to shield their team from the stress and the pressure of the upcoming board meeting or the ongoing raise. They assume that fundraising and board meetings are journeys they need to travel by themselves.

What I tell founders is that they are making a choice when choosing not to share investor challenges—either they are deciding that their teammates cannot help them with the problem or that they can’t handle the problem (i.e., it would be too distracting or destabilizing.) It’s their judgment call to make, but sometimes they might get it wrong and hold back from you precisely when you could have helped them or you could have handled it.


How to Act With Empathy:

  • Make sure that your expressions of appreciation for how your execs handle investors doesn’t end up in you taking them for granted.
  • If your executive cancels an important meeting with you because s/he is prepping for a board meeting, understand there’s something bigger than you going on here.
  • If your team is preparing to move into fundraising again soon, have an explicit conversation about how roles will shift temporarily while your founder/executive is focused on the round.
  • If you’re feeling annoyed about the lack of communication about how a round is progressing it’s not enough to just express that frustration and demand more. Instead, try inquiring about what is holding your founder back from sharing more. (A perception that you can’t help them? A perception that you can’t handle it?) And then if that’s something you can shift or clarify, try resolving it.


3) They choose to not do things every day that are super important.

You know how busy you are and how you often need to prioritize ruthlessly to get it all done? You might take a to-do list of 10+ things and pick the top 3 that will move the needle on your goals. You might cancel a meeting that wasn’t going to be that important anyways. You might just decide to not waste even 5-10 mins today on your Facebook news feed.

Well, your startup executives feel exactly the same way every day except that their “prioritization” process looks more like this: There are 100+ things on their to-do list and they will pick just 3 knowing that they are not picking the other 10 or 20 that might be equally as mission-critical or have as much needle-move-y potential. They are cancelling meetings about important topics with important people who they know will be deeply frustrated with them for postponing. And the idea of wasting five minutes on Facebook is actually funny to them because they might forget to eat, drink or pee today if someone didn’t remind them.

The higher one gets in an organization and the larger that organization grows the more time one needs to spend saying no or ignoring the less important. And that process of triage at work can be quite emotionally challenging. (To learn more about this for you and for your startup executive, check out Ed Batista’s post in HBR.)


How To Act with Empathy:

  • Realize that sometimes you are going to be the person, the meeting, the email that is super-important-but-not-top-3-important to your executive. This will be especially hard for you if you can remember a time when the team was smaller and when you were more important more often.
  • Understand that it’s uncomfortable and maybe even painful for executives to tell you that indirectly by not responding to your email or by canceling your meeting. But do not confuse importance with care or with value.
  • Mentally check yourself when you conclude that your executive “doesn’t care” about something based on your perception of their inaction. They might care or value this issue very deeply, but just not be in a position to display that care or act on that value today. They might be getting to it. They might be thoughtfully punting. They might be triaging other important needs first in order to set themselves up to act on it.


4) They are still surprised you take them so seriously.

Unlike their corporate counterparts who spend years or decades climbing the levels of organizational visibility to the top, startup executives face increased scrutiny from their employees and teammates almost overnight. But it will still take them a while to adjust.

They don’t realize how closely you watch them to see what they do and what they don’t do. They’re surprised to learn how carefully you listen to what they say and what they don’t say. And most are shocked to discover how much attention you pay to how they seem to feel on any given day.

And since they don’t assume you scrutinize them as seriously as you do….


  • To them it was a casual offhand comment, but to you it was a harsh joke that revealed how they really felt about your latest marketing campaign.
  • To them, it was a look of confusion over a change to a launch schedule, but to you that same facial expression was a look of scowling judgment that engineering is behind on deadlines again.
  • To them, it was an interesting blue-sky exchange about future product direction, but to you it was a last minute feature-request you need to push through the product and engineering teams now.


Every startup executive goes through an adjustment period when they learn how closely their comments, emails, behaviors and even nonverbals are observed and then reacted to throughout the team.

It is on them to learn that “impact rules” and that having a certain set of intentions in their heads is not sufficient.  They’ll learn to be more explicit about sharing their intentions or clarifying what they expect from an interaction or at least what they don’t want people to do. (Like saying: “Hey — this is just a chance to brainstorm together—please don’t interpret this as me requesting these features for the next release.”)


How To Act with Empathy: 

  • When you catch yourself (or other teammates) making inferences about your executives based on a single comment, a line of an email, a fleeting expression, a sarcastic quip—make sure to ask for clarifications.
  • Keep the window of interpretation open long enough that you can challenge your own inferences or, even better, so you can clarify intentions with the executive directly. Give them an opening to clarify: “How are you feeling about the change to the launch schedule? I think it would be helpful to the team to know how you’re taking this update in.”
  • Explicitly give them the benefit of the doubt and a second chance to clarify the impact they sought out to have:  “I’m guessing the comment at the end of the meeting was a joke—what were you trying to say about the marketing campaign?”
  • If you don’t have a chance to get an explicit clarification, try to challenge your interpretation on your own by extending the interval over which you’re interpreting. “She looked really unhappy at the end of that meeting. I wonder what’s up? Well, I know I’ve been in 3 other meeting with her this week and she was happy then, so I’m not going to read catastrophe into this…”


5) They often yearn for the old days when they could just put on headphones, block out the world, and code/build/design/dream for hours.

This one is particularly true for technical founders who used to be heavily involved in building product. But then the team grew and their role evolved (either slowly or suddenly) into enabling others to build. They now spend more time in meetings, more time with investors and more time with external stakeholders. While most do it with zeal and determination because that’s “what the company needs them to do” there is an unshakeable sense of loss. There is a yearning (often kept private) to go back to a simpler time.

Many founders, as they become startup executives, learn to embrace their new complexity. They get used to the so-steep-you-constantly-feel-you’re-backsliding learning curve of managing ever larger numbers of people. They rationalize to themselves how they can’t go back. They accept their new identity for its opportunities and its limits. But there is one thing they will likely still miss—and it’s one thing they can get back: pleasure.
There is pleasure in focused attention.


It just feels good to concentrate deeply and do something well. And so while the highest and best use of your executive’s time may no longer be to code or design alongside you—that doesn’t mean they can’t still take pleasure in focusing their attention on some other aspect of “building” the company.


How To Act With Empathy:

  • Don’t assume your executive team members are “too busy” to come to your team’s internal quarterly hacks. Invite them. They might still say no (see #3) but they’ll appreciate you think of them as people who can still build.
  • Tell them enthusiastically about what you’re building. And then tell them how much you enjoy what you’re doing. Many startup executives take deep personal pride in playing Chief Caveman or Cavewoman—running around gathering resources and keeping enemies away so the tribe can work safely, efficiently, productively and even joyfully back in the cave. Let them know you appreciate the effort, the sacrifice, and the choices they make so you can keep your headphones on, ignore the world, and build cool stuff.
  • And if you know they’re focused on building something (a board deck, the agenda for a leadership team offsite, a job description for a new hire, the company’s expansion strategy) try not to interrupt them. Gift them a few hours of focused attention. Offer to cancel a non-pressing meeting with you for them.
  • You can even suggest they set that boundary for themselves. Encourage them to work from home one morning a week and let them focus.


6) The joy they take in building the company is very real, but it’s usually not present in the moments anyone will write about, hear about or throw a party to celebrate.

I often hear nervous confessions from founders who “hate celebrations” or “loathe public praise” or “go to team parties to celebrate product milestones but secretly just wish they could go back to work.” Startup employees sniff this resistance out, but often misinterpret what they see and hear. They label their leaders as “too hard on themselves and others” or “downers” or “too serious.”

There are many possible drivers for this startup executive behavior. Sometimes founders (like many humans) actually feel a psychological discomfort with displays of positive emotion. Sometimes founders are so focused on taking a long-term view, that it’s difficult for them to fully see and appreciate a short-term victory. Sometimes executives worry (irrationally) that if they enable you to stop to party for a night that you won’t come back to work hard tomorrow. And sometimes it’s just hard to celebrate a legitimate win when they personally feel like they’re losing 9 times out of 10. Nevertheless, most founders will still put on a brave face and a smile and offer the toast at the celebratory happy hour. They congratulate you, and they do mean it sincerely.

But those moments aren’t likely what they would congratulate themselves on.

As a coach, I get a backseat pass to startups and the founder-executives who lead them and, yes, without a doubt I see a lot of struggle, stress, anxiety, depression, regret and painful, heart-wrenching learning.

But, I also get a front seat to Joy—and what I’ve learned is that the kinds of things that make founders and startup executives truly happy and feel a deep sense of fulfillment aren’t going to be found in press headlines. They aren’t a metric or milestone that anyone can see and then throw a party around. They usually happen in moments no one else would even notice.

Startup founder-executive joy is:

….looking around at a team they’ve built through hiring and firing and feeling tearfully proud of a culture that was cultivated from scratch

….standing up to a hostile investor and uncovering a new reservoir of emotional fortitude they didn’t know they had

….building something so truly excellent that customers volunteer to market it

….walking away from an acquisition deal that would have undermined their product’s mission

And there is joy in that ordinary moment on an ordinary work day when they look up from their laptop after years of slogging to realize that what once seemed like an improbable if not impossible dream…

It. Just. Came. True.

So, before you claim that your executives are grumpy hard-asses who never want to celebrate anything—challenge your interpretation of what you’re seeing. Yes, they might feel grumpy or act hard-ass-like at times, but it doesn’t mean their lives are without joy or they don’t know how to celebrate—they just might not be sharing that joy with you as you might expect.


How To Act With Empathy:

  • Don’t take it the wrong way when your startup leader appears to not want to celebrate something or doesn’t respond with unbridled enthusiasm to your suggestion that the team “should” celebrate a certain event or achievement. Even if they don’t share your sense of accomplishment at a personal or emotional level, it doesn’t mean they don’t think celebrations aren’t important and necessary for you and the rest of the team.
  • And don’t assume you do know what they will feel like celebrating. If you ever have the opportunity, ask them to tell you a story of the small startup moment when they felt most proud, celebratory and fulfilled—even if it was a glimmer, a fleeting moment or an otherwise unremarkable occurrence. You’ll probably be surprised (and maybe even moved) by what you learn.