Short answer
Choose someone who has sold in the field, not just someone certified by a training company. Look for a long-term engagement (at least one quarter, ideally a year), a regular coaching rhythm (around twice a week), work on your team’s live deals rather than slides, built-in reinforcement, and managers coached alongside reps. Ask how they’ll measure behaviour change, not just satisfaction.
Why the choice matters more than the content
Most sales methods sound sensible on a slide. The difference between a programme that changes your revenue and one that’s forgotten in a month is rarely the method. It’s who delivers it, for how long, and how close to reality they stay.
I’ve seen founders spend good money on polished workshops that left nothing behind. I’ve written about why in Why sales training is a waste of time (unless it’s reinforced). This checklist is the other side of that argument: what to look for so your investment actually sticks.
The checklist
1. Have they lived the field life?
This matters most. Your coach should have carried a target, sat across the table from customers, faced objections and lost deals. Certification from a sales training company isn’t a substitute.
Ask:
- Which companies did you sell for, and in what roles?
- What did you sell, to whom, and in which markets?
- Tell me about a deal you lost and what you learned.
A practitioner answers these with specifics. Someone who only teaches answers with frameworks.
2. Do they understand your ground reality?
Selling IT solutions through OEMs and distributors in India is different from selling SaaS in the US. Your coach should understand:
- how system integrators and solution providers make money;
- multi-level approvals, procurement and L1 pressure;
- the gap between a customer’s stated specs and their real business problem.
If the examples they use come only from American software companies, be careful.
3. Is the engagement long enough to change behaviour?
One quarter is the minimum. A year is better. Human behaviour takes time to change, and anything shorter is usually an event dressed up as a programme.
4. Is there a regular rhythm?
Look for contact around twice a week, not one long session a month. Short, frequent reinforcement beats long, rare sessions.
5. Do they work on your live deals?
The best coaching uses your team’s real opportunities: preparing for a meeting next week, reviewing a deal that’s stalled, rehearsing a negotiation that’s coming up. Practice on invented case studies is far less useful than coaching on deals that affect this quarter’s number.
6. Is reinforcement built in?
Ask exactly how a skill will be reinforced after it’s introduced. You want to hear about weekly reviews, pre-meeting coaching, follow-up on specific behaviours, and how the team will be held to the new standard.
7. Will your managers be coached too?
If your sales managers don’t continue the rhythm, everything fades when the coach leaves. A good engagement coaches managers to run the reviews themselves.
8. How will they measure success?
Avoid anyone who measures success with feedback forms. Ask what will be different in the field, and how you’ll see it:
- Is discovery being completed before proposals go out?
- Are opportunities qualified on clear rules?
- Is the forecast more accurate?
- Are reps less dependent on discounts?
Red flags
- A big launch event and little after it.
- Only PowerPoint, with no work on real deals.
- Generic content that could apply to any industry.
- No questions about your business before proposing a programme.
- Promises of quick results. Behaviour change takes months.
A quick comparison
| Look for | Be careful of |
|---|---|
| Field experience in technology sales | Certification as the main credential |
| One quarter minimum, ideally a year | One-off workshops |
| About twice a week | Monthly sessions |
| Your live deals | Invented case studies |
| Managers coached alongside reps | Reps only |
| Behaviour and forecast measures | Feedback scores |
Frequently asked questions
How long should a sales coaching engagement be?
At least one quarter, and ideally a year. Behaviour takes time to change, and the habit needs to survive after the coach steps back.
Is a certified sales trainer better than a practitioner?
Certification shows someone has learned a method. Field experience shows they’ve used it under pressure. For tech sales teams, practical field experience matters more.
How often should a sales coach work with the team?
Around twice a week works well: short, regular sessions focused on live deals, rather than long sessions spaced far apart.
What should a founder ask before hiring a sales consultant?
Where they’ve sold, what they’ll do in the first month, how skills will be reinforced, whether managers are included, and how success will be measured.
Looking for a practitioner, not a presentation?
Rajneesh has more than 2.5 decades in technology sales, including Ingram, IBM, Sun Microsystems and Oracle. Talk to him directly.
