How to hire sales reps without a mis-hire: what to listen for in the interview and the first 90 days

Most bad sales hires look great in the interview. That's the problem. Salespeople are good at interviews, because an interview is a sales meeting where the product is themselves.

So a process built on "do I like this person?" hires the best interviewer. A process that works asks them to do the job, in small pieces, before you hire them. This post is for a founder or manager with no recruiter and a team of 3 to 20, or none yet.

Before you write a word of the ad, write down the job. Answer these for yourself:

The line that trips most small teams is "where the leads come from". A rep who has only worked leads handed to them may struggle to find their own, so hire for the job you actually have.

Then write the ad from the profile, and put the hard parts in it: cold calling, weekend events, a target from month three. The people who apply anyway are the ones who'll stay.

The best small-team hires usually come from people you already know of. Job boards come last.

• Referrals from your team and clients. Asking "who's the best salesperson who's ever sold to you?" turns up names you'd never find on a job site.
• Reps at companies that sell to the same buyers. Check any non-compete terms before you approach them.
• People in customer-facing jobs outside sales, such as hospitality, retail or customer service, who are good with people and want to earn on results. They need more training and often stay longer.
• Job boards and LinkedIn, which bring volume and need a fast screen.

Whatever the source, screen with a 15-minute phone call: have they sold something like this, to buyers like these, the way you sell?

A good sales interview has three parts, and the middle one matters most.

Part 1: their record (20 minutes)

Ask about real deals, and keep asking what happened next.

• "Walk me through the last deal you won, from the first contact to signed."
• "Tell me about a deal you lost that you should have won. What would you do differently?"
• "What was your target last year, and where did you finish? How did the months go?"
• "Where did your leads come from, and how many did you find yourself?"

A strong rep remembers names, numbers and the moment a deal turned. A weak one talks about "building relationships".

Part 2: a role-play (20 minutes)

Give them a short brief a day ahead: who the buyer is, what you sell, what the buyer's problem is. Then you play the buyer on a first call.

Play a realistic buyer: a bit busy, brief with your answers, and ready with one objection you hear every week. Watch for:

• Do they ask questions before they pitch?
• Do they listen to the answers and ask a follow-up?
• How do they handle the objection? Do they get defensive, or ask what's behind it?
• Do they ask for a next step with a date?

Then ask them what they'd change about their own call. A rep who can see their mistakes is a rep you can coach. The cold calling script template makes a good brief for an outbound role.

Part 3: their questions (10 minutes)

Good reps ask about the leads, the target, how deals are won and who they'd learn from.

For your final two or three candidates, set one task that looks like the job and takes under two hours. Pay for it if it's longer.

• Write the first email and a follow-up to a real type of buyer you sell to.
• Research three companies from your list and say which to call first, and why.
• Listen to a recorded sales call (with permission) and write three things the rep could do better.

You're checking whether they can do the work and how they take instructions. Polished writing is a bonus.

Then call a former manager and ask two questions: "Would you hire them again?" and "What did you have to coach them on?" A pause before the first answer tells you a lot.

A vague answer about pay loses good candidates. Before you make an offer, write down:

• The base pay and the variable part.
• What counts as a sale, and when it's counted: signed, paid or delivered.
• When commission is paid, and what happens if a client cancels.
• The target for a ramped rep, and the lower target for the first months.
• Any cap or accelerator.

Keep it to one page and walk through a made-up month with them. The sales commission plan template has the sections. Don't promise what they'll earn; show how the plan works and let them do the sums.

A new rep's first three months decide whether they stay and succeed. Plan them before the start date.

• Days 1 to 30: learn the product, the buyers and the process. Sit in on calls. Make first calls on easier lists. No revenue target, but a clear activity number.
• Days 31 to 60: run their own first meetings with you listening in on some. A reduced target.
• Days 61 to 90: a full activity target and a partial revenue target. Weekly 1:1s about the numbers and one skill.

Sales rep onboarding has a week-by-week plan for the first month, and the 30-60-90 day sales plan gives the rep their own version to fill in.

Watch activity before results. A new rep who isn't making the calls by week six is telling you something, whatever they say in the 1:1. Ramp time explains how to step a target up month by month.

Scaling a sales team too early burns cash. Too late, and leads go cold. Hire the next rep when most of these are true:

• Your current reps are at or near target, and have been for a quarter.
• Leads are waiting. Enquiries sit for days, or reps have more follow-ups than they can make.
• You know how a new rep gets to target, because you've done it at least once.
• You can afford the new rep's ramp: several months of pay before they cover their cost.
• Someone has time to coach them. A new rep with no manager's time is a rep who leaves.

Hire two at once if you can, so you get a fairer read on whether the process or the person is the problem. Past five or six reps, somebody needs to manage the team as their main job. How to manage a sales team covers what that job looks like.

1. Write the profile from the job you actually have.
2. Ask your team and three clients for names before you post an ad.
3. Write a one-page role-play brief and a two-hour test task.
4. Put the pay plan on one page, with a worked month.
5. Plan days 1 to 90 before the start date.