The one question most strategists ask

As a strategist, my job is to ask questions—good, well thought out questions. Between spending my early career as a newspaper journalist and attending graduate school (not to mention developing complex strategies for Fortune 500 companies) I have been trained in the art of question formulation.

When I started teaching strategy in 2015, I was surprised by one of the most common questions most strategists actually have: Where do I start?

Whether speaking with fresh-out-of school strategists or well seasoned ones, this question has come up time and time again. And I could relate. Early in my career, when launching out on a strategy project, I often felt the same. There were so many questions to answers and so much work to do. Where does one start?

I propose there are two reasons why we, as the smart and curious professionals that we are, are asking that seemingly simple question.

• Projects can be complex. There is so much to learn, so much to know. In starting a strategy project, it often feels as if a firehose has been opened and it’s your job to take in an unending amount of often messy and incomplete data.
• We think we should know more than we do. We feel we should be experts on every new project. But while we may have experience in a specific industry, every project comes with a set of nuances that must be interrogated if we are going to produce work that performs.

Source: Hautestock

So, how do we answer this great mystery? I have your answer: You start with stakeholder interviews. Yes, simple one-to-one, conversations with your client or internal team are the answer. (Of course, you will have conducted a literary review of their documentation prior, but really, I see this as step zero.)

Here are the exact steps you’ll want to take.

1. Identify and schedule your stakeholders. Ideally, you’ll be speaking with three to 10 people for about 45 minutes each. Clearly you’ll be interviewing your main point of contact, but be sure to include their team and if needed, parallel team members touching the project.
2. Develop your stakeholder interview guide. Aim for about 15 to 20 questions that will not only give you key insights into the project but also how your client can win. What will they be reviewed on at the end of the year? What keeps them up at night? What do they need to know but don’t? What does success look like — for both you and them?
3. Conduct your interviews. You should be holding individual interviews, never group stakeholder interviews. This is crucial. If you would like to follow up stakeholder interviews with a workshop that is a fantastic next step, but do not undermine yourself by speaking to more than one person at one time. One person at a time means you will get more sincere, truthful answers and avoid group think or other influences.
4. Take great notes. I recommend Excel and I like to take all of my notes in one sheet so I can compare answers by question asked. It’s also great to record and transcribe your notes. I like Rev.com which is quick and affordable.
5. Finally, analyze and present your notes. Don’t skip the step of understanding where there is alignment and where there is discord. This is one of the most important findings for a strategist as well as the entire team. Create a presentation (just be sure to take out names) that summarizes your findings — especially the areas of disconnect — and present it back to your team as a discussion starter and foundation for future work. Also, revisit it before presenting your final recommendations.

Stakeholder interviews are your foundation for any good strategy. They are a relatively light lift and always so tempting to cut. However, skipping this step is fraught with problems because it leaves you guessing. And, as I like to say, in strategy, we don’t guess.

Your next step should include a workshop where you invite your stakeholders as well as a broader group of people. You can dive into some of the same issues you discussed during stakeholder interviews and expand from there.