Before you hire an AI strategy advisor, ask these four questions. The answers will tell you whether they can actually help you.
Question 1: What’s Your Operating Background?
Ask them to describe their operating experience:
- What teams have you built?
- What products have you shipped?
- What P&Ls have you managed?
- What organizational transformations have you led?
Look for real product and ecosystem scaling experience, not just consulting experience. Someone who’s had to live with the consequences of their recommendations will advise differently than someone who moves on to the next client.
LBZ Advisory brings operator-level experience from Microsoft and Qualcomm—scaling products, building teams, navigating organizational complexity. That experience informs every recommendation.
Question 2: How Long Does This Typically Take?
Ask them:
- How long is your typical engagement?
- What’s included in that timeline?
- How many workshops do you typically run?
- When do you hand off and what does that look like?
Look for 90-day engagements or less. If they’re quoting 6-12 months, be skeptical. Strategy doesn’t need to be perfect; it needs to be clear enough to act on. Speed matters.
Long engagements often create analysis paralysis. By the time the strategy is done, market conditions have changed.
What you want: A clear strategy in 90 days, then iteration based on results.
Question 3: How Do You Handle Constraints?
This is the real test. Ask:
- Walk me through a situation where a client’s constraints prevented a strategy you wanted to recommend. What did you do?
- How do you factor in organizational structure and decision speed?
- What if we don’t have the data quality we’d need? Do you start with what we have or wait for perfection?
- How do you design for what we can realistically execute?
Look for someone who acknowledges reality and designs around it, not someone who works in ideal scenarios and then blames you when implementation fails.
Ask them about the organizations where they’ve worked. Did strategy get executed? Or did it sit in a folder?
Question 4: What Happens After You Leave?
This is the most important question. Ask:
- How will my team execute this strategy without you?
- What training or documentation do you provide?
- How often will we need to call you back for questions?
- How do we measure if it’s working?
- Who on my team will own the strategy going forward?
The answer matters because consultant dependency is a sign the strategy failed. A good strategy is clear enough for your teams to execute independently.
If they’re hedging (“You’ll probably want to keep us around”) or vague (“We provide ongoing support”), that’s a yellow flag.
Bonus Questions: About Your Team
Ask about their team composition:
- Who will be doing the work?
- What’s their background?
- Will the senior person be involved throughout, or just at the beginning and end?
Also ask about their point of view. Do they have a clear methodology, or are they building from scratch for each client? You want someone with a repeatable approach, not someone who improvises every time.
The Leadership Skills Question
As you think about your AI strategy, also think about your leadership team’s AI fluency. Ask the consultant:
- What leadership capabilities do we need to build to execute this?
- Are you assessing our team’s readiness?
- What skills matter most?
Read more about the six research-backed leadership skills that differentiate real AI transformation from “AI theater”. An advisor should help you build these, not just hand off a strategy document.
What LBZ Advisory Answers
Here’s how we answer these four questions:
Question 1: Operator experience from scaling at Microsoft and Qualcomm, with deep product, organizational, and P&L background.
Question 2: 90-day engagements focused on clarity and decisions, not lengthy deliverables.
Question 3: We start with your constraints—your data, your teams, your operating speed—and design around them. We pressure-test everything.
Question 4: We leave behind a clear, one-page strategy your teams own. Documentation. Decision frameworks. Your team executes independently.
We’re here to make you stronger and more independent, not to create ongoing dependency.