Signs You Need a Product Strategist (And Signs You Don't)

A while back I gave a talk in Austin about product strategy for founders. After the session, several founders came up to me. Not to ask about frameworks or prioritization models. Almost every one of them asked the same question: “Should I hire someone to help me with product strategy?”

The honest answer I gave most of them: probably not.

Most startups don’t need a product strategist. They need clarity on what they’re actually trying to accomplish. That clarity sometimes comes from a conversation with someone experienced. Other times, it comes from customer conversations, focused thinking, or just doing the work.

After years of advising founders on product strategy, I’ve learned to recognize when outside perspective genuinely helps and when it’s a distraction from doing the real work.

Here’s how to know if you actually need outside product thinking help.

Signs You DON’T Need a Product Strategist

Let me start with when you should figure it out yourself.

Sign 1: You Haven’t Talked to Customers

If you haven’t had at least 15-20 conversations with potential customers, you don’t need a strategist. You need to validate your idea.

What’s actually happening: You want someone to tell you the idea is good without doing the hard work of learning if customers agree.

What to do instead: Talk to 20 people who fit your target customer profile. Ask about their problems, not your solution. The answers will give you more clarity than any strategist could.

Sign 2: You’re Looking for Someone to Make Decisions For You

Product strategy isn’t something you outsource. The founder needs to own strategy. A strategist can provide perspective, frameworks, and challenge your thinking. They can’t tell you what to build.

What’s actually happening: You’re uncomfortable with the uncertainty of making decisions, and you want someone else to be responsible.

What to do instead: Make the decision yourself. If it’s wrong, you’ll learn. That learning is more valuable than being told what to do.

Sign 3: You Haven’t Tried to Solve the Problem Yet

If you haven’t attempted to prioritize, haven’t tried different approaches, haven’t struggled with the problem, a strategist will just give you an answer you don’t know how to use.

What’s actually happening: You want to skip the learning process and jump to answers.

What to do instead: Try frameworks yourself. Read about product strategy and prioritization. Apply them. See what works and what doesn’t. Then you’ll know what questions to ask.

Sign 4: Your Problem Is Execution, Not Strategy

If you know what to build but struggle to ship it, you don’t have a strategy problem. You have an execution problem.

What’s actually happening: You’re hoping strategy advice will make execution easier. It won’t.

What to do instead: Fix your execution issues directly. Hire better. Ship smaller. Reduce scope. Get to working product, then worry about strategy.

Sign 5: You Want Validation, Not Perspective

If you’ve already decided what to do and you want someone to confirm it, you don’t need a strategist. You need to execute on your decision or admit you’re not confident in it.

What’s actually happening: You’re insecure about your decision and want external validation.

What to do instead: Either commit to your decision and execute, or honestly examine why you’re uncertain.

Signs You MIGHT Need a Product Strategist

Now for when outside perspective genuinely helps.

Sign 1: You’re Stuck at the Same Revenue for 6+ Months

You have product-market fit signals but growth has stalled. You’ve tried things. Nothing moved the needle.

Why a strategist helps: Fresh eyes see patterns you’re too close to notice. Someone who’s seen many startups can recognize common traps.

What to look for: Someone who asks hard questions, not someone who gives easy answers.

Sign 2: Your Team Can’t Agree on Direction

Strong opinions on what to build, but no consensus. Every planning session ends with “let’s do everything.”

Why a strategist helps: External perspective breaks political deadlocks. Frameworks create shared language for trade-off discussions.

What to look for: Someone skilled at facilitating decisions, not just making them.

Sign 3: You’re About to Make a Bet-the-Company Decision

Raising a round. Pivoting the product. Entering a new market. These decisions benefit from experienced perspective.

Why a strategist helps: Someone who’s seen these inflection points before can identify blindspots and help you think through scenarios.

What to look for: Someone with relevant experience. “I’ve seen 10 startups make this pivot” is more valuable than general advice.

Sign 4: You Don’t Know Why You’re Building What You’re Building

Roadmap full of features, but no coherent story connecting them. Can’t articulate how today’s work leads to tomorrow’s outcomes.

Why a strategist helps: Helping connect features to strategy is specific expertise. Most founders are good at features or strategy, rarely both.

What to look for: Someone who thinks in systems, not lists.

Sign 5: Your Customers and Data Tell Conflicting Stories

Customers say they love the product but churn. Metrics show growth but revenue doesn’t follow. You’re drowning in information but starving for insight.

Why a strategist helps: Making sense of conflicting signals is a skill. Experienced product thinkers have pattern-matched across many situations.

What to look for: Someone who digs into your data and talks to your customers, not someone who gives advice without context.

What a Good Product Strategist Actually Does

Let me demystify what working with a product strategist looks like.

What They Do

Ask hard questions you’re avoiding

“Why do you believe customers want this?” “What happens if you’re wrong about that assumption?” “What would need to be true for this to work?”

Provide frameworks for thinking

Not answers, but ways to think about problems that reveal new options.

Challenge comfortable assumptions

The beliefs you’ve held so long you forgot they’re assumptions.

Identify patterns from experience

“I’ve seen five startups try this. Here’s what worked and what didn’t.”

Create clarity from confusion

Help you see what you already know but haven’t articulated.

What They Don’t Do

Make decisions for you

A good strategist clarifies options and trade-offs. You still decide.

Write your roadmap

They might help you think about prioritization. They shouldn’t create your plans.

Guarantee outcomes

Anyone promising results is selling snake oil.

Replace doing the work

Strategy without execution is worthless. They can’t ship for you.

How to Get Value Without Hiring Someone

Not ready for a strategist? Here are ways to get similar benefits.

Option 1: Find Founder Peers

Other founders at your stage face similar challenges. Regular conversations provide:

• Fresh perspective
• Accountability
• Pattern matching from their experience

Where to find them: YC alumni network, Indie Hackers, founder Slack groups, local meetups.

Option 2: Advisory Board Conversations

Advisors are essentially informal strategists. One conversation per month with the right advisor provides perspective without cost.

How to find good advisors: Look for founders 2-3 stages ahead of you who’ve solved problems you’re facing.

Option 3: Customer Immersion

Spend a full week only talking to customers. No building. No planning. Just conversations.

You’ll emerge with clarity that no strategist could provide, because it comes from direct customer contact.

Option 4: Strategy Sprints

Set aside 2 days to focus entirely on strategy:

• Day 1: Diagnosis. What’s actually happening? What are the real problems?
• Day 2: Options. What could you do? What are the trade-offs?

No execution. No interruptions. Just thinking.

Option 5: Read and Apply

Much of what a strategist provides is frameworks. You can learn these yourself:

• On strategy: “Good Strategy Bad Strategy” by Rumelt
• On product: “Inspired” by Cagan
• On prioritization: “Escaping the Build Trap” by Perri

Read with your specific situation in mind. Apply the frameworks to your problems.

What to Look For If You Do Hire

If you’ve determined you need outside help, here’s what to look for.

Green Flags

Asks more than tells

Good strategists ask questions to understand your situation before offering perspective.

Pushes back

If they agree with everything you say, they’re not adding value.

Relevant experience

They’ve seen problems like yours before. Not just “20 years in product” but specific relevant experience.

Clear process

They can explain how they work, what they’ll deliver, and how you’ll measure success.

Makes you smarter

After working with them, you should be better at product thinking yourself, not more dependent on them.

Red Flags

Promises specific outcomes

“I’ll increase your retention by 50%.” Nobody can promise that.

Cookie-cutter frameworks

Uses the same approach for every company without customizing to your situation.

No track record

Can’t point to specific results from previous work.

Advice without understanding

Gives recommendations before deeply understanding your business.

Creates dependency

Wants ongoing retainers without clear deliverables. You should need them less over time, not more.

The Honest Truth About Product Strategy Help

Here’s what I’ve learned from both sides of this conversation:

Most founders don’t need a strategist. They need:

• More customer conversations
• The courage to make decisions
• Focus on fewer priorities
• Permission to ignore distractions

Some founders genuinely benefit from:

• Experienced perspective at inflection points
• Frameworks for thinking about hard trade-offs
• Help seeing patterns they’re too close to notice
• A thinking partner for bet-the-company decisions

The difference isn’t about company stage or funding level. It’s about readiness. If you’ve done the work and you’re genuinely stuck, outside perspective helps. If you haven’t done the work, outside perspective is a procrastination tool.

Questions to Ask Yourself

Before seeking outside help, honestly answer:

1. Have I talked to at least 20 potential customers?

If no, do that first. It’s free and more valuable than any strategist.

2. Have I tried to solve this problem myself?

If no, try first. The struggle creates learning that makes advice actually useful.

3. Can I clearly articulate what I’m stuck on?

If no, you’re not ready for outside help. You need to clarify your own thinking first.

4. Am I willing to hear that my assumptions are wrong?

If no, you don’t want strategy help. You want validation. That’s different.

5. Will I take action on what I learn?

If no, advice is wasted money. Only seek help when you’re ready to act on it.

FAQ: Product Strategists and Advisors

What’s the difference between a product strategist and a product manager?

A product manager is embedded in your team, owning day-to-day product work. A strategist provides outside perspective, usually on specific questions or timeframes. PMs execute. Strategists advise. Most startups need the former before the latter.

How much should product strategy help cost?

Varies widely. Informal advisor conversations: free to equity-only. Project-based consulting: $5K-50K depending on scope. Ongoing advisory: $500-3000/month. Quality doesn’t correlate directly with price.

Can a strategist help with technical product decisions?

For technical decisions (architecture, tech stack, etc.), you need technical expertise, not product strategy. These are different skills. Some people have both, but make sure whoever you talk to has relevant technical experience.

How do I know if the advice is good?

Good advice feels uncomfortable at first. It challenges your assumptions. If everything someone says confirms what you already believed, they’re not adding value.

Key Takeaways

• Most founders don’t need a product strategist. They need customer conversations, decision-making courage, and focus.
• Signs you don’t need one: Haven’t talked to customers, want decisions made for you, haven’t tried to solve the problem, need execution not strategy, or want validation.
• Signs you might need one: Stuck at same revenue for 6+ months, team can’t agree on direction, bet-the-company decision coming, no coherent strategy story, or conflicting signals from data and customers.
• A good strategist asks hard questions and makes you smarter. They don’t make decisions for you or guarantee outcomes.
• Before seeking help, try: Founder peer conversations, advisor relationships, customer immersion, strategy sprints, or learning frameworks yourself.

What’s Next

Start by honestly answering the five questions above. If you’ve done the work and you’re genuinely stuck at an inflection point, outside perspective might help.

If you haven’t done the work yet, do it. Talk to customers. Try frameworks. Make decisions. The struggle is where learning happens.

And if you’re at one of those inflection points where a thinking partner would help — let’s talk. I don’t tell founders what to do. I help them think more clearly about what they already know, then build the thing with them.

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Related Reading:

• Product Strategy for Early-Stage Startups - Start here if you want to develop strategy yourself
• How to Validate a Startup Idea - The customer conversation framework
• When to Hire Your First Product Manager - Different from a strategist
• Feature Prioritization When Everything Feels Urgent - Frameworks you can apply yourself