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On Leadership: Execution

September 26, 2022

This is a guest post written by Bolster Prime Mentor Tim Enwall.

Execution makes all the difference for practically every startup. It’s a core risk venture capitalists evaluate.

Forces arrayed against startup leaders are well-known and myriad: capital constraints, lack of brand awareness, lack of distribution, unequal access to labor, and, until the growth stage, foggy notions about product-market fit. Why add an inefficient and chaotic execution engine that, at best, could be described as a cacophony of effort and, at worst, flat-out disorganization?

When it comes to week-to-week, month-to-month execution, most startups, especially first-time startups, “just wing it”. They operate by feel and without a whole ton of communication about what they’re doing and why. The “what” comes out in dribs and drabs. A leader may convey ideas with urgency and importance, but without connecting the dots within the bigger picture. Often, startups find themselves overwhelmed with work because it just keeps piling on without any rhyme or reason.

As a company scales, more and more people get frustrated because they lack context or information about priorities.

This common cacophony of effort often causes teams to focus more on anything that seems urgent, and less on strategic initiatives. The result is more people doing ineffective, unimportant, duplicative work.

Or, said differently, waste.

In this mode, a raft of questions typically emerges from those who are performing the work:

  • Why are we doing what we’re doing?
  • What is the “larger picture” (the vision? the mission?)
  • What are we really trying to accomplish?
  • What’s the highest priority accomplishment? (What can we de-prioritize?)
  • What is a successful outcome? What’s an amazing/”wow!” outcome?
  • How will we know we’ve achieved that outcome? (What will it mean if we don’t achieve it?)
  • Who is making decisions about each priority or outcome?
  • Who is responsible for driving the outcome? Who is required to participate? Do they have other higher-priority responsibilities?
  • What is needed to achieve the priority or outcome? Do we have the required elements? Or do they need to be procured and/or redirected from a different priority or outcome?
  • And on and on…

These questions always get answered because we, as human beings doing work, want them answered. However, they might be answered verbally, passed inefficiently from one person to another in a game of telephone. They might be written down, but stored and shared in a piecemeal fashion—often in Slack or some other messaging system.

Experienced and foresighted startup leaders recognize that these questions are always present and choose to write the answers down in an organized fashion. Why? To keep a corporate record and to promote:

  • Clarity of purpose, outcome, and priority
  • Focus
  • Knowing where we are against an outcome
  • Decision-making (higher priorities come first)
  • Stress relief

There is some effort that comes with the practice of recording information in an organized fashion. Ultimately, though, the rewards far outweigh the effort.

Common Execution Systems

So, what are the best practices for recording information, answering questions, and creating execution systems? At the end of the day, the best system is the one that works for your company. There are, however, some common solutions that have worked for many teams before, and I suggest you start with these.

Mark Benioff (CEO, Salesforce) created V2MoM. In its very first year of operation, John Doerr (Intel/Google Advisor) helped the four person team adopt OKRs. Mark and John were both experienced startup leaders who created written systems to answer the myriad of questions team members asked. Most notably, they started at the beginning and, unquestionably, achieved insane levels of success.

V2MoM stands for “Vision, Values, Methods, Obstacles, and Measures”. You can read a lot about V2MoM on the web and many companies large and small have adopted them as a standard practice. As it implies, Vision starts with a very long-term perspective for the company—the ultimate objective being pursued.

  • Vision: a long term perspective; the ultimate company objective
  • Values: core company principles
  • Methods: primary outcomes, meant to assure the vision
  • Obstacles: key barriers to be overcome
  • Measures: indicators of completion of the primary outcomes (Methods)

While Vision and Values are difficult to cascade down into an organization, Methods, Obstacles, and Measures can be (note: many organizations of size do ask their middle managers to create functional Visions). They can be narrowed down to fit each team’s specific focus.

OKR stands for Objectives and Key Results. For more in-depth information, this Perdoo article is an excellent practical summary.

  • Objectives: outcomes to achieve
  • Key Results: measures to determine when objectives are achieved

OKRs explicitly incorporate the concept of a Project (or Project, Task, Work Item, or any other word that connotes a fairly bounded piece of execution), as you can see in the article linked above.

V2MoM’s long horizon and concise structure make it a fantastic annual planning tool. For the same reasons, it’s great for communication with Boards of Directors. It is harder, though, to use it for short term planning, since it lacks detail at the project level. OKRs are a bit easier to use from a week-to-week, month-to-month perspective.

The important thing is to create an execution system that truly works for your organization. There is no one correct way to do it, since every team is different. At Fermyon, we’ve combined the best of V2MoM and OKR, since they overlap in clear ways and provide useful content for everyone, from individual contributors all the way to the Board of Directors.

For an excellent, practical example of how we implement our execution systems, visit my blog!


Execution matters. It creates a harmonious orchestra of startup contributors who have excellent clarity of purpose, priority, effort, commitment levels, ownership, and continuous improvement. It allows for the maximum utilization of the talents and energy of every startup member—as opposed to some meaningful percentage of wasted effort and increased frustration.

There’s a reason Salesforce and Google implemented explicit, extensive, and written down execution systems—they wanted that harmonious orchestra and, ultimately, they wanted the same startup prize that all of us want: amazing success. Not all startups will have amazing success, but those with explicit execution systems are certainly more primed for success than those with wasteful chaos as their system.

-Tim Enwall, September 26, 2022.

Tim Enwall is a four-time startup CEO with several successful exits and a passion and focus on extraordinary teamwork. Currently working with Fermyon, leading the third wave of cloud computing.

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