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How to Kick Off Any Strategic Initiative With Success

Kick off your strategic initiative with intention to avoid common mistakes and save time in the long run.

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In my 14 years leading strategic initiatives of all kinds, I see leaders make the same mistake time and time again. There is little-to-no intention during kick off. This typically results in missed milestones, goals, and dysfunction. Have you already kicked the can on any of the strategic initiatives you had teed up for this year? Chances are you have — and you’re not alone. 

There is an exercise I've developed over the past five years that's allowed me to kick off any strategic with great success. I’ll admit, there have been times that I have been so eager to jump into an initiative that I've skipped my own best practice. And each time I did, chaos insued. Certainly validation of the framework, right? Because of this, I wanted to share this framework so that other entrepreneurs can benefit from the results I have experienced. 

Related: How to Grow Your Business With Intention

First, before I jump into the details of the framework, let’s talk about the team: the group of individuals you’d assign the execution of a strategic initiative. I highly recommend capping the group at five people. I’m not referring to the entire group involved in the initiative — that could be as large as your entire company. I’m only referring to those that are accountable for the success of the initiative. 

What types of roles should these team members play? The most important is the group lead, who should be a talented facilitator. This can be a project manager, but there can only be one group lead. Your team should also include someone accountable for hitting milestones on time with their associated deliverables, typically a project manager. Other roles can include subject matter experts or leaders of certain functional areas, someone in charge of , and all the doers. 

Now that you’ve identified your team, let’s dive into the exercise framework. The entire purpose of the exercises is to properly scope the initiative, gain alignment, build buy-in across the team and provide tools to resolve conflict. Dedicating this time to the front end will save time and headache over the long run.

I recommend budgeting at least one hour and being prepared for some tough conversations and disagreements. The point is to get these disagreements out in the open and dealt with before execution begins. 

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Be sure to set the purpose and intention for the session by explaining the benefits I’ve described. When scheduling the session, the group lead should share that they will be leading the team through a discussion and documentation of the following topics:

  1. The mission of the strategic initiative

  2. Roles and accountabilities

  3. The to be done

  4. Key stakeholders

  5. Assumptions

  6. Dependencies 

  7. Desired outcomes

  8. How to measure success

  9. A team contract describing how to work together

A co-working document should be created and shared with editing access to the entire team. It should act as a contract between the team and each member should feel they had a voice in completing it. 

Before any other topic can be discussed, especially solutions, the team must align on the mission of the strategic initiative. What are you trying to achieve and why? It should certainly align with company business goals, the mission of your company, and align with your values. 

Defining roles and accountabilities can be the hardest part. Try the first draft before discussing anything else related to the initiative, and then circle back to them to see if they’ve changed by the end of the exercise. I find they typically do, but you should draft them first to determine what assumptions your team members have made regarding their roles. In my experience, many people get their role at the company and the role related to the initiative very confused, so be prepared to explain the difference. 

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Now that you’ve aligned on the mission and have roles and accountabilities drafted, you can start listing the work to be done. This is high level and should be turned into a project plan after completing the exercise with success. You may find one of those steps includes defining business requirements.

Next, you will want to list all of the stakeholders related to the initiative. Who is the ultimate decision-maker? Who should be included in communications? Who all should have a voice in any proposed solutions?

Defining the assumptions can be the toughest part. Try having each person describe the reality that must exist for this initiative to be successful. It certainly needs to be a priority, have a budget and be possible with given constraints. Determine what assumptions might need to be validated with your stakeholders for the initiative to be successful. 

Dependencies are typically easy, but double check you’ve listed all of them — even the obvious ones. What does the team need to accomplish all of the work to be done? What work will block the completion of other work?

It is critically important to align on what success looks like related to your initiative. A simple way is to describe the desired outcomes post-execution. You'll want to be sure to understand how those outcomes can be measured and if there's a baseline of to measure success against. If not, add that to the work to be done.

This is when you will want to go back and revisit those roles. Tighten them up a bit with newly achieved clarity. Perhaps you’ve even discovered that you have the wrong group entirely and you just saved the initiative from utter failure. 

Related: How a Fractional Executive Can Take Your Business to the Next Level

Lastly, have the team sign a contract regarding how they will work together throughout the planned period. Have them agree to the following:

  1. Their roles and accountabilities are clear. 

  2. How they choose to communicate, when and where.

  3. What decisions they anticipate having to make and the decision-making process. 

  4. How conflict is resolved and the escalation process. 

  5. How to share feedback with one another. 

  6. The meeting rhythm for the initiative, or the cadence for getting the work done and check-ins. 

You must leave time for this last part — it’s the most important! If you skip it, you are making dangerous assumptions and have missed the entire purpose of the exercise.

There you have it: my framework for kicking off a strategic initiative with success. I hope it brings you as much value as it has in my career.

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