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The value of distributed strategic planning

Chase Damiano
17 min read
The value of distributed strategic planning

There was a time when everyone looked to me and the CEO for every answer. We were at the center of everything in the business—for the worst.

As a COO, I bridged the strategic vision of our CEO and operational execution of our team.

Every week, the CEO and I met one-on-one to share what was top of mind. We kept great rapport and synchrony. Given our vantage point, we could assess, decide, and act quickly. We could consider input from investors, advisors, founder peers, macro-market indicators, and regional trends. The vision was clear in our minds’ eyes, as we could “see” the future of the company unfolding. And we could move fast and in flow.

And as fast as we could dream, the day-to-day shows up to burst our idyllic bubble. A team member asking for a pay raise. Another drops a keg and breaks their toe. A surprise health inspection. An unhappy customer. An investor phone call. Dozens of “tactical” issues pulled us back into the here and now. Turns out, nothing grounds you from aspiration to reality faster than a critical team member submitting their two-week notice.

There’s a reason for the adage, “Ideas are worthless. Execution is everything.” We can dream all we want—but without enacting the vision into reality, it remains an illusory image. Dreams are unrealized potential, and you can’t build a company on ideas.

Image 1
this shark gets it.


​The pressures founders face

In the earlier stages, founder/CEOs either set priorities and goals in isolation or with very few additional voices. The process? Clear their schedule, head to a quiet place, reflect and process what they’ve learned, and set new goals for the coming interval. Maybe your process is different (or perhaps you don’t have one—that’s okay too).

But this strategy breaks down as you build a team.

Think about it: The team members you hire are likely leaving safer, better compensated, more structured (and likely boring, uninspiring, meaningless, and disempowered) jobs to come work for you—willing to trade this for the excitement, chaos, and opportunity of your start-up.

And what luck! You hear the magic words, “I’m willing to do anything.” A smart, hungry, motivated generalist who wants to grow and learn? Every founder’s dream!

So, who is this teacher, who will grow and develop this individual? That’s you.

You might start by handing off some basic responsibilities and priorities. Perhaps to free up your plate, perhaps because their expertise is better than yours. You’re off to the races together. And look! Positive results! It’s working! More trust, more delegation, more ownership. Things are going great! Business is doing well, so let’s hire a few more people.

More people means more horsepower, but it also means more complexity and exponential growth in the number of relationships on the team. More problems to solve, but it’s manageable. Not everything is perfect, but you feel good and continue along.

But, given this rise in complexity, what started as crystal clarity transforms into foggy ambiguity. Where you’re going, what to do (and NOT do) and how to do it once felt clear. Now, you find yourself saying, “I have to think about that” and “let me get back to you.” Why? More complex decisions, higher stakes, more people, and more long-term implications. Imagine how this compounds: more team members looking to YOU for guidance, support, training, coaching, problem-solving, decision-making… quickly leads to getting bogged down.

Everything from simple decisions and requests like:

  • Where can I find that document?
  • Can you take a look at this and give me some feedback?
  • I need to talk to you about something—have time for a quick call today?
  • Have you thought about our last conversation about X topic?
  • Are these results any good?
  • I’m stuck—where do I go from here?
  • John isn’t responding to my messages; can you talk to him?

To longer-term questions like:

  • Where are we really heading as a team?
  • What opportunities are available down the road?
  • What is the benefits and compensation plan?
  • Should we optimize for growth or efficiency right now?
  • What’s the exit strategy?

All of a sudden, you’re stuck at the center of your company, bottlenecking the growth of the organization because everything comes through you—especially the most difficult, open-ended, challenging, and hairiest questions.

the oh-so-uncomfortable feeling of bottlenecking growth


​This is a natural waypoint in the journey of an entrepreneurial leader.

The path to alignment

The solution? Clarify and create organizational context as a strategic asset that pays you dividends in the form of speed, time, effectiveness, retention, and focus.

  • Speed = faster time to big milestones, like profitability, the next fundraise or liquidity event
  • Time = more of your time spent on vision, growth, and new opportunities
  • Effectiveness = improved quality of product or service in less time
  • Retention = customers/users stay longer; employees stay longer; poor fits exit faster
  • Focus = fewer big priorities instead of a thousand small ones

This is a solution of communication, and there is a sliding scale of approaches to create this organizational context.

On one end of the spectrum, you go off into your cave and you “think about the goals.” Then, like an angel descending from the heavens, you share the good word on the vision and goals, expecting praise, inspiration, and motivation to spontaneously erupt in our teams. “Let’s do this! RAHHH!”

On the other end, you leave it entirely to your team to create their goals, and like a train with no tracks, the direction can be anything: no coherence, complete siloing, no teamwork or connectivity. Some song and dance, box-checking exercise. Goals to have goals. As the leader of the company, you are agnostic and removed to the output of this (they aren’t the real goals anyway).

Today, I’m sharing the middle road: distributed strategic planning.

What is distributed strategic planning?

This is about getting in a room with your team, and harnessing the collective wisdom in the room to co-create the vision and goals.

Experimenting with team vision and goal-setting methodologies over the last decade, and supporting dozens of founders with this process hands-on, here are a few things I’ve discovered:

  • Top-down goals are quick, speedy, intuitive, and connected to the bigger picture. All the planning happens rapidly. But what you gain in perceived speed (process is done faster), you lose in communication. Like a broken record, you must instill the vision and goals in every member of the team. Why it’s important, the implications, the impacts.
  • Bottoms-up goals are disconnected, slower, and can be meaningless. The process can be disorganized. No one really cares. No one is bought in, and the exercise isn’t valuable. But, it’s a step in the right direction to get others involved in planning and thinking about the future.
  • Co-created goals, with distributed strategic planning, are collaborative, accurate, and decisive. All the planning can happen rapidly, and the communication is built-in. The process is built to allow everyone to share ideas, contribute, and leave feeling aligned—regardless of the content of the goals. Execution can be much quicker with a team bought-in and ready to act.

Think about this: with an organization of dozens, hundreds, even thousands of people, do you believe that the founder/CEO is using the same communication paradigm as they did when they were a smaller company? Hell no. They’ve cultivated a strong leadership team, a bench of advisors and mentors, and a way of collaborating and listening to their employees to guide their decision-making.

I advocate for founder/CEOs to involve their teams in strategic planning earlier than they would think. Why?

  • It gives a 360 view of the organization, at all operational levels, to surface challenges, opportunities, and blind spots.
  • It gives those who took a bet on you a unique opportunity to contribute at a higher level. This secures loyalty, buy-in and tenure—and they can’t get that opportunity anywhere else.
  • It exposes your team to your thinking, ideas, and motivations earlier in the company’s history. This allows them to tune in with you and generate better, more unique ideas—building a culture of experimentation.
  • It yields an opportunity for leaders to be more vulnerable: admitting that you don’t have all the answers. (You don’t have all the answers; you’re just being honest about it). This builds psychological safety—a predictor of team learning behaviors and team performance.
  • It offers a “let the best ideas win” culture. The organization isn’t betting on any one person (ahem, YOU) to “figure it out.” Instead, it distributes the challenge of vision and strategic planning more widely to the organization.

Worried about losing control or making the “wrong decisions?” That’s natural. You’re still the founder/CEO and at the end of the day, you can still decide what makes the list (and not). But instead, you’re engaging your team to create a first-draft, leaving you mental space to be the editor. Big difference.

Based on extensive survey data from my clients, teams that experiment with this methodology consistently report feedback such as:

  • I feel our company’s top goals and measures of success are clear.
  • I feel a sense of camaraderie, alignment, and unity within the leadership team and my direct reports.
  • I believe these are the right goals for our company, department, and me.
  • My individual views are well-represented in the goals.
  • I feel accountable to the goals assigned to me.
  • I feel engaged and motivated at work.

​The evolving paradigm of great leadership

This begs a question: If we’re co-creating the goals as a team, then what is my role as a leader?

The next generation of leaders are those who are curious, empathetic, attuned to their teams, and care about their development. This is not about what we do; this is about who we are and how we relate to our people. This is the long-term bet I’m making, by investing into leaders today who are actively cultivating the gift of generating other leaders.

Leadership is not about taking power. It’s about giving power.

Will you step into your vulnerability as a leader? Will you answer the call to inspire and lead your team?

Tell me—who will you be?​

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