As a startup junkie, I’ve seen it many times before. Your infant company (your baby) demands your total commitment. It’s your primary concern and total responsibility 24/7.  Feed me…I’m yours. Then, one day, your baby is a teenager, and you’ve never been more delighted and terrified at the same time.

You evolve from seat-of-the-pants, all-hands-on-deck, git’er done management style to developing and optimizing strategic business processes. You revisit your startup culture and original vision to determine if they hold up and can support the company long term.

By your teenage years, you have customers and employees, as well as investors, contractors, vendors, community stakeholders, industry leaders, and even competitors all vying for your attention and time. 

You’ve survived the Terrible Twos when seemingly everyone was running with scissors. Now people have opinions and thoughts and feelings. They often act independently of you. And they all have expectations of you and oftentimes unrealistic expectations. 

Somehow you must meld all this into a cohesive company.

Welcome to the teenage years—that period when you’re no longer truly a startup but growing and maturing, and still doctoring the occasional scraped knee.

Lessons From My Teenage Children…The Stakes Just Went Up

I wish my children would not grow up and remain teenagers forever…said no parent ever.

My kids have always looked on me as the “fun one.” The one who plans vacations.  The one who thinks school needs to be balanced with life experience. The one who takes them to movies and concerts on school nights.  Gives them a second bowl of ice cream when Mom isn’t looking. I’m still the fun one but holding on to that reputation by a thread these days. I’ve noticed that I’m playing the dictator a bit more as my three daughters entered their teenage years.

Case in point: Two months ago, sitting around the dinner table, my daughters were trying to argue their preference for an event with friends rather than a previously planned ‘educational’ event for the whole family.  They were trying to wear me down through a barrage of insult after insult hoping that the teenage equivalent of toddler pouting would sway my conviction like it did when they were adorable.

Right there, in front of my kids…in front of my wife…in front of myself…I turned into my Dad. Out of my mouth came the words that fathers have uttered since the days of Noah: 

“I’ve had enough. The decision has been made and we’re done. You may not understand why I’ve made it, and I don’t even care if you disagree with it. It’s what we’re doing. Because your Mom and I are the adults and you are our responsibility at the moment.  Maybe someday you’ll understand, but even if you never do, I’m okay with that too. End. Of. Discussion. Now pass the damn salt.”  

Damn.  Did I just flip into that mode?

Parenting three teenage daughters is reinforcing how important it can be to get this phase right. I’m walking a tightrope between supporting their decisions and laying down the law. And you see in your every action—as well as in theirs—the potential for huge, life-altering implications of decisions.  The stakes are too high to not provide guard rails and bumpers to keep them from unknowingly hurting themselves. How did we ever survive our youth?

Every day is a challenge and most seem endless. Life has gone from cute and fun to just plain serious and sometimes difficult.

Luckily, I have teenage daughters at home who have prepared me for the challenges of startup adolescence.

The Teenage Startup Dilemma

So how does coping with and corralling teen daughters inform my management style when dealing with a maturing startup?

The big ah-ha in our household of the teenage transition is that I have to accept that I won’t be well-liked most of the time.  There is a growing gap between what my teens want from me and what they need. My wife and I have to be OK with this uncomfortable tension and confident that our wisdom will get our daughters on the right path to adulthood.

And it’s this same tension between wants-and-needs that is presenting itself in our growing teenager startup these days too.

The Big Five Gaps

For over 10 years I’ve been a part of the senior team at growing startups.  Mostly A and B-round funded companies trying against the odd for meteoric growth.  As with my teenage daughters, I’ve noticed this same gap of wants-and-needs between senior management and others at these startups.  It’s frustrating for all involved but also very common. When staff approaches me needing to vent or seek counsel, I try to suppress my smile and reassure them ‘This, too, shall pass.  We’ll get through it.’

I’ve noticed 5 common wants-and-needs gaps that are common for teenage startups.  Between the handful of startups at which I’ve worked and the other dozen in which I’ve invested or advised, these gaps are almost as predictable as struggling to find the teenage balance of screen time and reacting to the first boy-girlfriend at home.  

So whether you are management or managee, know that what you are experiencing is normal and common – and that others before you have successfully navigated this minefield that feels paralyzing at times.  

The gaps include:

Cheerleader v. Realistic Optimist: People expect company leaders to always be shouting encouragement and doing backflips…no matter what. We could be in the fourth quarter, with sales down 30 points from the plan with no way to catch up, but people want management cheering them on.  Telling them there is a ray of hope that we’ll pull off the quarter. Sometimes one’s circumstance just doesn’t have a success path and no matter how positive and insightful, leadership can’t manufacture one out of thin air. Being expected to always shake your pom-poms can be emotionally draining and just plain unrealistic, which may be why I’m mostly no good at it.

Progress has ups and downs, and things are never as good (or as bad) as we think. So don’t get carried away with either extreme. It is certainly important in the roller-coaster of startups to find the silver lining, but also don’t expect your management team to hand out rose-colored glasses.   Being a truth-teller, albeit a positive one, is a very important perspective to bring to your growing startup. Painting a vision of a possible future needs to be balanced with operating within the realities of the business.

ER Doc v. Teacher: For whatever reason, people typically refrain from coming to senior management when they have a problem—particularly a customer-related problem—early enough for that experienced team to help. Instead, staff often waits until a relationship is flatlining or a circumstance is terminal. They panic and call management in expecting them to get out the paddles and raise Lazarus from the dead. It doesn’t work that way.

Although I support decentralized decision-making, when people call us in at 11:59:59 pm, they can’t expect management to reverse the momentum or turn back the clock. Operating in a crisis mode, like an Emergency Room, doesn’t maximize good outcomes.  If you bring management into situations too late, all they can often do is try to turn disaster into a teachable moment. Consider involving your most experienced management early before a situation goes off the rails to ensure the best results. Practice prevention rather than expecting miracles.

Marxist-Socialist v. Oligarchy: I believe in an open environment and sharing an abundance of information throughout the organization. I want staff to see the continuity of our decisions as well as the consistency between what the senior team tells them and what we say in the boardroom. As an example, we share our Board meeting presentations with our entire staff so folks are assured that our messaging and strategy is consistent across all stakeholders.

But sometimes this candor can backfire. People may interpret openness with the entitlement to question everything and request to know the logic behind all decisions. In reality, NDAs, confidential information, private investor information, and competitive opportunities prevent full disclosure in many circumstances. This limits the cohort of people who have all the information that went into a particular decision or strategy.  And makes answering pointed questions in a satisfying manner a challenge.

Understand that staff shouldn’t be left out of the major decision-making and deserve to participate in idea generation.  At the same time, allowing input is different than delegating responsibility and decision making. Share what you can with all staff, but also know when to draw the line…and hope that if you are consistent enough in your decision making over time, people will trust you to do the right thing even if they sometimes don’t completely understand or agree with management in every circumstance.

Validation v. Empathy: Similarly, while we try to create an environment that’s incredibly participative and inclusive, sometimes people will expect you to bow to their strong opinions. You can’t always do so.  Someone might be passionate and loud, but it doesn’t make them right. All points of view are not equal, and relativism in decision making can splinter your organization and might plunge it into chaos.  As an example, LeadGenius recently initiated a major design change to how we align staff to prospects and customers. The reaction approached anarchy. The senior team spent over a month listening to folks who were convinced we would destroy the business and had a litany of suggestions on other ways to solve the problem.  We listened intensely and showed compassion, but our ultimate decision did end up disappointing some.  

While you should provide a platform for ideas, you can’t validate everyone. Senior management must determine what it’s willing to take on and is compensated well to make tough calls. Even though some individuals will disagree or be disappointed, management must consider its obligations to all stakeholders, make the hard decisions and act for the greater good.

Director of Fun v. Fulfillment: An employee recently said, “Mark, I don’t think people are having fun. We need to do something.” CEO as social director…really?  I never knew that providing fun was an employer’s obligation. It’s possible that every generation defines Maslow’s Hierarchy of Needs a bit differently, but it wasn’t many decades ago when a satisfying job meant putting food on the table and a roof overhead.  I worry that the tech-bro culture and wild financial inflows drowning San Francisco is warping the expectations of staff who have only worked in an economic cycle of abundance. It hasn’t always been ping-pong tables, bean bags, Patagonia jackets, private transportation, and unlimited food.  And I suspect this ‘fun’ won’t last forever.

All employees, senior management included, work on behalf of a company’s owners-investors (of which staff can be with stock options) and customers.  It’s serving the desires and needs of these stakeholders that must be paramount.   In this pursuit, employers should provide a respectful environment in which people can be challenged intellectually and learn.  If that isn’t fun to you, you might need to seek it elsewhere.  

Lyrics of a Lifetime

In the year of my birth, Mick and Keith released a sing-along anthem that closed the decade on the turbulent 1960s with the chorus:

You can’t always get what you want
But if you try sometimes, well, you might find
You get what you need.

As with my growing daughters, so too with teenage startups…never have truer words been written.  If you manage or work in an awkwardly growing startup, appreciate The Stones wisdom and embrace their relevance.  And go ahead – hum along too.