Why Good Strategy Takes Time to Measure—On the Court and in Business

This past Fall, my wife and I coached our children in youth sports.

I coach our seven-year-old’s baseball team, and my wife Emily coached our nine-year-old’s volleyball team.

Real quick, you should know about my wife: she’s good at volleyball. She was the captain of her high school team, and we played in adult leagues in and around New York City when we were in our 20s, where Emily was clearly the greater asset for our coed teams despite my standing seven inches taller.

Many nine- and ten-year-old girls are just beginning to learn the fundamentals of volleyball, making it a challenging age group to coach.

It’s not as hard to watch as “beehive” kiddie soccer or enduring a game of four-year-olds distracting themselves for an entire tee-ball game, but volleyball is a tough sport to learn for younglings, and therefore not the same high-octane event it becomes as they get older and smash the ball downward.

Still, my wife drew on her years of volleyball training to instill fundamentals and a disciplined approach with the kids. Rather than only focusing on how to serve and how to hit the ball back over the net (the two focal points of most of the other parent coaches), my wife taught the kids proper form for how to pass and set the ball, proper footwork, and the most basic “play” in volleyball: pass the ball to the setter, don’t just hit it back over the net.

Her team’s skills improved rapidly, and as the season progressed, it was clear these kids were making strides far beyond the kids on other teams and were having a blast while winning most of their games. Winning wasn’t the point—building skills, positive habits, and confidence were the goal. The kids’ parents, to a family, all wanted their kids on my wife’s team again the following season, thanking her profusely for investing in their development.

When the playoffs came around… they lost in the first round. Ouch.

The coach of the other team had coached their players up in a simpler, easier to implement strategy: just get the ball back over on the first touch.

So while my wife and daughter's team play was more elegant, the other team's strategy was more practical when you consider the skill level of 9 year olds who have trouble mastering accuracy and teamwork, but can get the ball over the net reliably and wait for mistakes from their opponents.

Alignment Takes Practice

Passing to a specific person requires more skill than just aiming to put the ball somewhere over the net. There is a higher risk of errors when you have a second and probably a third kid involved getting the ball back over.

You’ll see no Olympic team just hitting the ball back over the net on the first touch, though. That would be a losing strategy, and it would get ugly quickly. But for the nine-year-olds coached to do it in the YMCA league, it was a splendid strategy for just winning a game or this season’s trophy.

The highest levels of performance in team sports like volleyball requires players to be in sync with each other at multiple levels:

• Strategy - Which play are we running? How do we react to different situations?

• Timing - The setter and attacker need to be totally in sync; a fraction of a second ruins a chance to score.

• Specialization - I can spike a lot harder than my wife, but she is far more accurate with her setting. Reversing these roles would harm the team.

• Trust - Understanding situations where your teammates can be expected to succeed, and acting accordingly.

These traits don't come at a team level overnight. They require a lot of practice.

They also require effective leadership.

Alignment Takes Leadership

The level of alignment that leads to peak performance doesn't come about naturally. The six best volleyball players can't step onto the court and expect to be successful without getting in sync. “Bye, Bye, Bye” to that team's chances of winning (I'm so sorry, I couldn't help myself).

As the leader, like a sports coach, the job is:

• Determine the strategy

• Set the lineup

• Train the team

• Hold players accountable

If I'm not doing these things, I'm not really the leader. I might be the owner, delegating these outcomes to a different leader, or abdicating leadership if I haven't selected and empowered anyone to perform them.

Strategy Needs Time to Cook

Not all strategies yield immediate results. Some require patience and persistence to show their full impact.

Investing is a good analogy. If you walk into a financial advisor's office and tell them you want to plan for retirement, they will clarify your goals, consider your age and income level, and set up a plan to help you achieve your desired retirement finances. But if your goal is to double your money this week, or make $10 Million in the next five years, you'd be in the wrong place. Maybe you can try to double your money this week at a poker table, or build a $10 Million bank account in five years by building and selling a successful business.

Another analogy: a lasagna takes twenty minutes of prep time plus an hour to cook in the oven, so you're looking at quite some time before it's ready to eat, but a hot pocket will be ready to eat in about 90 seconds. Both deliver dough, cheese, and sauce to your mouth hole, so if that's your KPI and you want to achieve it as quickly as possible, go burn your mouth on the hot pocket.

Even proven leaders need time to implement a strategy effectively, as success is often built over time rather than appearing instantaneously. On the other hand, unproven leaders require even more patience and space to develop their credibility and demonstrate their effectiveness. The challenge, however, is distinguishing between a strategy that needs more time to mature and one that is simply not working. Knowing when to persist and when to pivot is a crucial skill for any leader, whether in sports or business.

Choosing Speed vs. Alignment

There is no universally right or wrong strategy—only strategies that fit different goals and time horizons. Leaders must assess their objectives and choose an approach that aligns with their vision and timeline.

• Speed may be necessary when facing short-term constraints or needing rapid iteration.

• Alignment requires more upfront investment but leads to stronger long-term performance.

• The right balance depends on the nature of the challenge—short-term survival vs. long-term dominance.

Whether coaching a youth volleyball team or leading a business, understanding the trade-off between speed and alignment can be the difference between fleeting success and sustainable excellence.

In my earlier days as a founder, I was sometimes frustrated when mentors wouldn't give a straight answer to a strategy question but would instead keep asking questions. I've come to take it as a sign of good insight. Now, I'm skeptical of people who always have a cut and dry answer about strategy without clarifying the goal. Expecting an immediate return on investment from long term strategies is a flawed leadership characteristic. When I observe that type of leader, they strike me as that annoying pickup volleyball player that thinks they are a hero for hitting the ball over the net quickly.

The earlier a startup or the smaller the team, the more often Speed should be top consideration, or else the long-term plan is moot. When it comes to developing youth who will take their skills and habits up to the next division with them, then it makes sense to teach fundamentals they can use later, not just optimize for winning the kiddie league. Same goes for business leaders who want a strong group of employees to rely on in the long term: we need to invest in their development, giving them the room to fail and learn.

This is different from "lowering the bar", which would be to change the definition of success, akin to participation trophies. Instead, you're setting your time horizon for those success metrics like you would when hiring a professional sports coach: if an organization is hiring a new head coach every single season, the problem is likely not the coaches, it's the ownership. If you want to develop a team for long term success, often the right move is to trust the right leader, align on the real goal, and let them cook.