Strategy Session Questions: What to Ask Before You Decide

The quality of a strategy session depends heavily on the questions you bring into it. Whether you're meeting with a coach, a mentor, your business partner or your whole team, the right questions turn a pleasant conversation into a decision you can act on.

This guide is a question bank for owners, organized by stage: what to answer before the session, what to ask during it and what to settle afterward. You won't use every question every time. Pick the few that fit the decision in front of you.

Before the session: frame the decision

Most strategy conversations drift because the decision was never named. Spend 20 minutes answering these on paper first:

• What decision am I actually trying to make, and by when?
• What happens if I make no decision at all?
• What options am I already considering, and which one am I leaning toward?
• What do I know for sure, and what am I assuming?
• What information would most improve this decision, and can I get it before we meet?

For the information question, public data can help. The U.S. Small Business Administration's guide to planning a business points owners to federal statistics for market research and competitive analysis, including the U.S. Census Business Builder, Census Bureau demographics and Bureau of Labor Statistics data.

Questions about where you compete

Roger Martin, writing in Harvard Business Review in 2014, argues that two choices determine success: the "where-to-play" decision (which specific customers to target) and the "how-to-win" decision (how to create a compelling value proposition for those customers). Those two ideas generate some of the most useful questions you can ask:

• Which customers do we serve better than anyone else nearby, and why?
• Which customers cost us more effort than they're worth?
• If a new customer chose us over a competitor, what would the reason be?
• Is that reason something we can keep doing well as we grow?

Michael Porter's 1996 Harvard Business Review article "What Is Strategy?" adds another angle. Porter describes strategy as the creation of a unique and valuable position and argues that a sustainable position requires trade-offs. In his words, "The essence of strategy is choosing what not to do." So ask:

• What are we choosing not to do?
• Which requests do we say yes to that pull us away from our best customers?

Questions that test the logic

Martin's article also urges leaders to make the logic behind their choices explicit. He frames it as a question: for your choices to make sense, what do you need to believe about customers, about the evolution of your industry, about competition and about your capabilities? He stresses writing the answers down, because people tend to remember events as having unfolded according to plan.

Turn that into four short questions for each option on the table:

1. What would have to be true about our customers?
2. What would have to be true about how our industry or market is changing?
3. What would have to be true about how competitors will respond?
4. What would have to be true about what we can do well?

Then ask which of those beliefs you're least sure of, and how you could test it cheaply before committing. For example, imagine a small fitness studio considering early-morning classes. One belief is that enough members want a 5:30 a.m. slot. A two-week pilot with a sign-up sheet tests that far more cheaply than hiring a new instructor.

Questions that hunt for blind spots

In a 2006 Harvard Business Review article, Max Bazerman and Dolly Chugh describe "bounded awareness," a phenomenon that causes people to ignore critical information when making decisions. You can push against it with questions like:

• What information would change my mind?
• Who would disagree with this plan, and what would they say?
• What are we not looking at because it's uncomfortable or hard to measure?
• What did we decide last time that didn't work, and did we understand why?

A premortem works well here too. Gary Klein, in a 2007 Harvard Business Review article, describes having team members assume the project has just failed and then generate plausible reasons for its demise. Ask: "It's a year from now and this went badly. What happened?"

Questions about capacity and commitment

A strategy that ignores your capacity is a wish list. Before you commit:

• What will we stop, pause or slow down to make room for this?
• What will this cost in cash, and what will it cost in the owner's hours?
• Who owns it, and do they have the time and authority to do it?
• What is the first visible step, and can it happen in the next two weeks?
• What early signal would tell us it's working, or that it isn't?

After the session: lock in what you decided

End every strategy conversation with a few closing questions, and write down the answers:

• What exactly did we decide?
• What is still open, and who will bring it back, by when?
• What are we telling the rest of the team?
• When will we review this decision, and what will we look at?

Keeping a short decision log with your reasoning also gives you something to compare against reality later, which is the point Martin makes about recording your logic.

Using these questions with a coach

If you're working with a strategy coach, bring two or three questions from this list to each session rather than all of them. A good coach will often ask some version of these on their own, and will push back when your answers are vague. Your job is to arrive with the decision framed and the facts gathered, so the time goes into thinking rather than catching up.

Key takeaways

• Name the decision and its deadline before any strategy session.
• Ask where you'll compete and how you'll win, and what you're choosing not to do.
• For each option, list what would have to be true, then test the shakiest belief cheaply.
• Hunt for blind spots by asking what would change your mind and running a premortem.
• Close every session by recording what was decided, who owns it and when you'll review it.

Sources

• Roger L. Martin, The Big Lie of Strategic Planning, Harvard Business Review (January–February 2014)
• Michael E. Porter, What Is Strategy?, Harvard Business Review (November–December 1996)
• Max H. Bazerman and Dolly Chugh, Decisions Without Blinders, Harvard Business Review (January 2006)
• Gary Klein, Performing a Project Premortem, Harvard Business Review (September 2007)
• U.S. Small Business Administration, Plan your business