Hiring a sales coach can be one of the best decisions you make for your business.

Or it can be a frustrating waste of time and money, and cause a significant setback in your company’s momentum. 

The right coach helps you win better customers, shorten sales cycles, build a repeatable revenue engine, and make you a better business leader. 

The wrong one? You’ll still be ghosted by buyers, still wondering why that pilot didn’t convert, and still working weekends to fill the pipeline.

So how do you choose the right sales coach?

Here’s what to think about before you sign on with any sales coach — especially if you’re in healthcare or health tech.

1. Does the coach know your industry?

This is non-negotiable. Sales coaches love to say, “Sales is sales.” But when you’re selling into hospitals, health systems, or health plans, that’s not that simple. In fact, it’s a morass or complexity, upheaval and dysfunction:

• Billing codes, reimbursement models, and RCM workflows

• Credentialing, compliance, and regulatory oversight

• Multiple stakeholders (clinical, operational, financial)

• Sales cycles with more turns than a patient referral form

If your coach doesn’t understand that, you’ll spend more time explaining acronyms than improving your win rate.

Look for someone who already speaks your language. They should know the jargon. Be up to speed on market trends. Understand how value gets communicated differently to a medical director versus a VP of population health. Bonus points if they have existing contacts or have navigated similar buyers before.

Bottom line: in health tech, the ability to navigate “how the system works” is a sales skill. Your coach should have it.

2. Do they have experience in adjacent markets?

Healthcare expertise is key — but some variety in background is actually a good thing.

If they’ve sold in industries like financial services, telecom, or pharma, they’ve likely developed a strong grasp of the rigor, process, and compliance-driven sales execution required in other verticals. That insight and experience can translate well to the transitions being inflicted on healthcare’s interrelated and overlapping systems and workflows.

For example, UnitedHealth Group hired senior execs from banking and finance for precisely that reason: the attention to process, the ability to manage large, high-risk transactions, and the intense focus on customer experience.

Personally, I’ve sold to pharma, individual providers, PBMs, telecoms, and financial services companies — and that context helps spot patterns, see opportunities to pivot, and challenge assumptions.

A coach with some breadth often sees solutions where others don’t.

3. Do you actually like the coach?

It may sound obvious, but this is crucial.

You’ll be spending time with this person. Letting them into your sales calls. Your pipeline. Your wins—and your misses.

They’ll be disagreeing with you. Challenging your assumptions. Asking tough questions.

You want that — but you also want someone who communicates clearly, listens closely, and makes the process feel supportive.

A great coach is:

• Encouraging, but not enabling

• Honest, but not harsh

• Creative, but still grounded

So be sure to ask yourself:

• Do you enjoy brainstorming with them?

• Do they help you think more clearly?

• Would your team benefit from that energy and guidance?

If the answer is yes, you’re on the right track.

4. Do they bring tools, processes, and frameworks?

Good coaches don’t wing it. They’ve seen patterns, developed frameworks, and built tools that help accelerate your progress.

Maybe it’s a better call structure. A deal qualification template. A messaging framework for navigating health plan RFPs.

These assets aren’t just helpful — it signals they’ve done the work, with a thorough grasp of sales as a craft, and they have a repeatable system to guide you.

And the best part? You can often repurpose these tools across your team, so even junior reps or new hires benefit.

5. Do they have expectations?

A good coach isn’t just showing up for the hour.

They’re invested in your success.

That means they have expectations for you — like reviewing calls, trying new approaches, or following up with customers.

They’ll gently push you to stretch.

They’ll challenge you to hit milestones.

They’ll notice if you’re not doing the work.

You should want that. Because change is hard. Sales is emotional. And the healthcare sales cycle rarely gives you instant feedback.

The right coach will help you stay on track, even when it’s tough.

6. How are they at breaking down problems?

Selling in B2B health tech means solving layered, often ambiguous problems.

Does the coach approach challenges with curiosity and flexibility?

Do they explore why something isn’t working — not just tell you what to do?

The best coaches don’t offer quick fixes. They provide thoughtful options, break down the trade-offs, and give you ways to test and validate.

You want someone who thinks with you — someone who seriously considers your ideas, explores alternatives, and helps you decide based on real-world constraints.

7. How strong are their communication skills?

Your coach shouldn’t just be able to sell. They should help you communicate better, too.

Look for someone who can:

• Critique your sales deck or proposal

• Sharpen your email copy or LinkedIn messaging

• Role-play discovery questions or pricing conversations

In health tech especially, clear communication is everything.

You’re explaining new models of care, integration steps, reimbursement impact, and outcomes measurement.

Can your coach help you make that story compelling?

8. Are they responsive?

This is simple — but overlooked.

Can you get time with them when you need it?

Customer engagement happens in real-time. Decisions often get made on timelines outside your control. Being nimble and responsive should be one of your competitive advantages.

And your coach should be prepared to accommodate those demands. If it  takes days to reply to a text or you can’t book a session until next week, that’s not helpful.

Look for someone who:

• Sets expectations about availability

• Is reachable between sessions (for quick check-ins or deal advice)

• Shows they’re in the game with you, not just clocking hours
  
  

9. Do they love what they’re doing?

Is this their main gig — or are they just picking up coaching work until their next role?

Sales coaching isn’t a side hustle. It’s a commitment.

A great coach is constantly refining their thinking, developing new ideas, and staying close to the field.

When you talk to them, you should feel it:
- They’re energized. Engaged. Curious.
- They love helping people get better at sales.

That energy is contagious. And it’s exactly what you want in your corner.

In Summary...

Hiring a sales coach is an important decision.

Done right, it’s an accelerant — for your skills, your team, and your revenue.

But it only works when there’s a fit. And that means:

• Industry expertise

• Actionable tools and resources

• Good communication and collaboration

• Mutual trust and follow-through

This is especially true in healthcare sales, where sales cycles are long and the sales process is complex. Being selective and deliberate are required.

If you’re considering a coach — or just exploring what that kind of support might look like — I’d be happy to talk. No pressure, no pitch. Just a conversation to see what you’re working on and whether coaching makes sense.

Let’s chat.