Running strategy interviews: guiding questions, process, and analysis
Ten to 35 conversations are what separate a pile of numbers from a real diagnosis. Who you talk to, how you ask, and why anonymity isn't negotiable.
By Christian Underwood ·

What are strategy interviews for?
They're the qualitative part of your situation analysis. The numbers show what happened. The conversations explain why, and they make visible how differently members of the leadership team read the same situation.
The line that nails it is in the book: if you don't ask, you don't want to know. The experience behind it: in almost every company, someone has had the decisive information for a long time and was never asked.
For the people you interview, these conversations are also a signal. Being asked before a decision is made feels entirely different from having a result presented to you. That's not a side effect, it's one of the reasons the effort pays off.
Across several conversations, patterns emerge that no data set can produce on its own. Three people from three different areas name the same root cause independently. That's a stronger finding than any single opinion in the room.
Who should you interview?
A full 360-degree view is ideal and often not feasible given time or budget. In that case, work from the inside out.
- Internal key people. The leadership group involved comes first, ahead of every other group.
- Important internal and external stakeholders. Owners, advisory board, employees in key roles, important suppliers.
- Active customers and non-customers. The second group is the most valuable one and is almost always skipped.
- Outside experts. People with a view of the market who have nothing to lose.
How many people per group depends on your size. In a company with 150 employees, eight internal and six external conversations is a workable split. More important than the split: make sure at least one person on the list is someone you expect an uncomfortable answer from.
Non-customers are worth the effort. Customers explain why they stayed. Non-customers explain why they decided against you, and that's the information that actually changes a strategy.
How many conversations, and how long?
Ten interviews at minimum, 35 at most. Past that, the analysis effort climbs sharply while the insight barely grows: the patterns repeat.
Dimension | Benchmark | Reason |
|---|---|---|
Number | 10 to 35 | Beyond that the patterns repeat while the effort keeps rising |
Length per conversation | 45 to 90 minutes | Shorter stays on the surface, longer wears out both sides |
Conversations per day | fewer than four | Listening is harder work than talking |
Total duration including analysis | 6 to 8 weeks | Scheduling, conducting, transcribing, coding |
Spread the conversations across several weeks instead of bunching them together. After the first five interviews, your follow-up questions change because you've started to notice patterns. Run all of them in three days and you give that effect away.
The most common planning mistake concerns the analysis. It takes more time than the conversations themselves, and it's routinely budgeted at zero days.
How do you run the conversations?
As a dialogue, not a questionnaire. A pure question-and-answer routine feels like an interrogation to the person across the table, and the answers are guarded accordingly.
Four ground rules make the difference: a clearly defined time frame, openness and neutrality on the part of the interviewer, strict anonymity of the results, and destruction of all recordings after the analysis. The last two are not a formality. Without them, you'll get the answers people think you want to hear.
One question belongs at the end of every conversation: what should I have asked you? It reliably opens up exactly the topic the other person has been waiting for the whole time, and that appeared in no interview guide.
In the conversation itself: ask open questions, keep probing with a simple "why," and above all, listen. The guiding questions set the frame; within it, the conversation can go where it goes.
One point that's easy to overlook: if you interview employees, clarify in advance whether the works council has to approve. And no one can be forced into an open conversation, participation is voluntary.
Which guiding questions belong in the interview guide?
A guide is not a script. It makes sure the same topics come up across fifteen conversations, so the answers can be compared later. Within those topics, every conversation can take its own path.
The guide follows the modules of the situation analysis, so the answers end up where they're needed later. In our experience, these questions carry the furthest.
- Customers. What's different today compared to yesterday in terms of expectations? Which segments do we address, and which do we deliberately not address? How well do we serve the most important needs compared to the competition?
- Market and competition. Where is the greatest potential today and tomorrow? Who are our competitors, how profitable are they, and what drives their profit?
- The new rules of success. Which trends matter most to our industry, and how are they changing the factors that drive success?
- Environment. What's affecting us from the economy, society, geopolitics, demographics, and regulation?
- Our own reality. What do the five-year trends in our key figures look like, and what explains them?
Say two things at the start of every conversation: why you're talking and what happens with the results. Both take a minute and noticeably change the quality of the answers.
How do you analyze the interviews?
In four steps. First, the recordings are transcribed. Then the statements are grouped along the modules. Next they're coded, meaning tagged with recurring keywords, so that clusters become visible. Finally, the findings, along with selected verbatim quotes, feed into the modules of the situation analysis.
Keep the analysis separate from the judgment. First collect what was said; only then does the team assess what holds true. Mix the two and you'll filter out uncomfortable statements before they ever made it onto the table.
The quotes are more than decoration. One anonymous sentence from a conversation carries more weight in a workshop than any summary, because it can't be argued away.
Watch for dissenting voices when you group the answers. The temptation is strong to extract the majority view from fifteen conversations and treat the rest as outliers. It's often the single dissenting statement that hits an untested assumption inside the company.
Store the results so they can still be found a year from now. The interview analysis is the only document in the entire process that explains why a decision was made. When the strategy gets reviewed, that's exactly the file people will look for.
Use software for the coding. It's tedious work, and that's precisely why it's the step where manual effort produces the most errors.
Common questions about strategy interviews
How many interviews does a situation analysis need?
Ten to 35. Beyond that, the patterns start repeating while the analysis effort keeps growing. More important than the number is the spread across internal and external interviewees.
Who should conduct the interviews?
Someone neutral, someone people can speak openly with. In smaller companies, that's hard to staff internally, because everyone in the building depends on management.
Why does anonymity matter so much?
Without it, you get filtered answers. Anyone who worries that a critical statement will be traced back to them will say what's safe, and exactly those statements are worthless for a strategy.
Should we interview customers as well?
Yes, and non-customers above all. Customers explain why they stayed. Non-customers explain why they decided against you, and that's the more valuable information.
How long does the analysis take?
Longer than the conversations. Plan six to eight weeks for interviews and analysis combined, depending on the number of conversations and how many people are interviewing in parallel.
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