The Side Car Hiring Playbook

You've probably hired the wrong salesperson before.

This is the process that stops that from happening again. Practical, direct, and written for owners who don't have time for expensive mistakes.

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Most bad sales hires don't happen because the owner wasn't paying attention. They happen because hiring for sales is genuinely hard, and most of the advice out there is written for companies with a full HR department and a three-month runway to figure it out. This playbook is written for everyone else.

The hiring mistake that happens before the first resume arrives

Most owners think they get hiring wrong in the interview. They don't. They get it wrong before they write the job posting, when they sit down to describe the role they wish they were filling instead of the one they actually need to fill.

 

Here are the signs you've done this before.

01

You hired someone who interviewed well

And couldn't perform once they were in the role. The conversation was great. The output wasn't.

02

You've had the same conversation twice.

New rep, same problems three months in. Different person, same outcome.

03

Onboarding a new rep takes forever

Because everything they need to know lives in your head. There's no written process to hand them.

04

You're not sure what you're actually hiring for.

Hunter or farmer? New business or account growth? You'd describe it differently on different days.

05

Good reps leave and take their momentum with them.

The pipeline collapses when someone walks out the door because it lived in their relationships, not in a system.

If any of those land, the problem isn't who you hired. It's the process you used to hire them. A better process won't guarantee a perfect hire. It will significantly improve your odds and stop you from making the same mistake twice.

The best hiring process isn't the most thorough one. It's the most repeatable one. Repeatable beats inspired on a bad day every single time.

If you've made the same hiring mistake more than once, the process needs a look.

Side Car works through hiring directly with clients, building the profile, the process, and the evaluation framework before the next search starts. That's a much better conversation to have before the hire than after it.

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Build the profile before you write the posting

Before you write a single word of a job posting, you need to answer five questions honestly. Not aspirationally. Honestly.

What does this person actually need to do?

Not eventually. In the first six months. Be specific. "Drive revenue" is not a job description. "Make 40 outbound calls per week, manage a pipeline of 30 active prospects, and close 8 to 12 new accounts per month" is a job description. If you can't write it down with that kind of detail, you don't know what you're hiring for yet. Stop and figure that out first.

Is this a hunting role or a farming role?

These are different skill sets. A hunter finds new business from nothing. A farmer grows and retains what's already there. Most owners say they want both. Fine. But if you had to weight it 70/30, which way does it go? That answer changes who you're looking for.

What does your sales cycle actually look like?

A rep who thrives on fast transactional deals will struggle in a six-month consultative sale. Know your average deal length, your typical decision-making process, and how many people are usually involved. Hire someone whose natural tempo matches your reality, not the one you wish you had.

What does good look like in your environment?

If you have a strong performer already, use them as a benchmark. What do they do that nobody else does? How do they handle a deal that stalls? You're not cloning them. You're trying to understand what success looks like in your specific context before you try to find it somewhere new.

What will make this person fail?

Think about the last hire that didn't work out. What was the real reason? Skill? Work ethic? A process that was never documented and they needed more structure than you could give them? Being honest here keeps you from making the same mistake with a different face.

Write a posting that filters, not attracts

Most job postings are written to attract as many applicants as possible. That's backwards. You don't want volume. You want the right three people in your inbox, not seventy who sort of fit. A good posting does your filtering before you spend a minute of your time.

Lead with what makes this hard

Don't open with how great your company is. Open with what the role actually demands. If it requires cold outreach, say it. If the territory is underdeveloped, say it. If there's no established brand recognition and they'll be introducing your business to people who've never heard of it, say it. The right candidate reads that and thinks: that's the kind of challenge I want. Everyone else self-selects out. That's the goal.

Be specific about money

Posting "competitive compensation" wastes everyone's time. Give them a range. If you're offering a base of $55,000 to $65,000 with an OTE of $90,000 to $100,000, say that. Candidates who want something different won't apply. Candidates who are a fit won't wonder if they're wasting their time. Vague compensation attracts people who assume the best and get surprised. That's not a great way to start a working relationship.

Include a small task

Ask them to do something minor in the application. "In 100 words or less, tell me about a deal you lost and what you'd do differently." You'll immediately filter out everyone who doesn't bother. The ones who do tell you something about how they think, how they handle failure, and whether they can write a coherent sentence. That last one matters more in a sales role than most owners expect.

Screen fast and cut early

The phone screen exists for one reason: to save time. Yours and theirs. Keep it to 20 minutes. You're not making a hiring decision here. You're answering one question: is it worth spending 90 minutes with this person?

Four things to listen for on a phone screen

Can they tell their story clearly? If they can't explain their own career in a way that makes sense, they probably can't explain your product to a prospect.

Are they asking you questions? Good salespeople are curious. If they're not curious about the role or what success looks like, pay attention to that.

Do they know their numbers? Ask what their quota was, what they hit, and what their conversion rate looked like. Candidates who can't answer this either haven't been measured or aren't being straight with you.

How do they talk about leaving their last job? You're not looking for perfection. You're looking for self-awareness. Someone who blames everything on external factors is showing you how they'll explain a bad quarter on your team.

If the screen goes well, move them forward the same day. If it doesn't, end it cleanly. Don't drag out a process for someone you already know isn't right.

Interview for coachability, not just confidence

This is where most owners get tripped up. Salespeople are trained to sell themselves. The most polished candidate in the room is not always the best hire. Confidence is easy to perform. Coachability is hard to fake, and over a two-year employment relationship it matters a lot more.

Questions on self-awareness

Tell me about the worst sales slump you've been in. What caused it and how did you get out?

What feedback have you received more than once that you've struggled to act on?

Describe a time a manager told you something you disagreed with. What did you do?

Questions on process

Walk me through how you'd approach a brand new territory with no existing pipeline.

How do you prioritise when you have more opportunities than you can work?

What does your pre-call preparation actually look like?

Questions on fit

What kind of manager brings out your best work?

Where do you want to be in three years, and does this role actually get you there?

That last question matters more than people give it credit for. A candidate who wants to be VP of Sales in three years when you have no intention of building that structure isn't a bad candidate. They're just a wrong fit. Better to find out now.

Give every finalist a real scenario

Something like: "You've been with us 60 days. You have a list of 50 prospects and no warm introductions. Walk me through your first two weeks." You're not looking for a perfect answer. You're looking for structured thinking, realistic assumptions, and a willingness to ask clarifying questions before diving in. A candidate who immediately launches into a detailed plan without asking you a single question is either overconfident or not listening. Neither is great.

This is usually where the process falls apart.

Most owners get to the interview stage, feel good about a candidate, and move fast. The hard questions don't get asked. The reference check becomes a formality. And three months later you're wondering what you missed. If you want help building an evaluation process that's actually repeatable before your next hire, that's a conversation worth having now rather than after.

Book a call with Mark
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Check references like you mean it

Reference checks are the most underused tool in the hiring process. Most people treat them as a formality. They're not. Stop asking questions designed to get a recommendation and start asking questions that surface real information.

Questions that actually work

On a scale of 1 to 10, how would you rate their performance? What would it take to get to a 10?

Would you rehire them today? If not, why not?

How did they handle feedback when they disagreed with it?

What's something they need to work on that they may not be fully aware of?

Anyone who gives you a 10 immediately isn't paying attention. Listen for the gap between the number and the explanation. Also notice who they refer you to. If every reference is a peer or a friend rather than a manager, ask why. Request a direct manager from their most recent role specifically. If they can't produce one, that's worth understanding before you make an offer.

Make the offer and set up for success

Be direct. Give them a number and a deadline. "We'd like to offer you a base of $60,000 with an OTE of $95,000, and we need a decision by Friday." Don't leave it open-ended and don't apologise for the number. If it's right, it's right. Know your range in advance and decide before the conversation whether you're willing to move. Negotiation on a job offer is normal. Being unprepared for it isn't a great look.

 

The first 90 days matter more than the first day

This is where the second biggest hiring mistake happens, right after the first one. You make a great hire, throw them in the deep end, and wonder why they're struggling at month three. Before someone starts, you should be able to answer: What are they learning in week one? Who are they meeting in the first two weeks? What does a successful 30-day mark look like? If you can't answer those questions, you're not ready for them to start.

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A good hire who gets a bad onboarding can look like a bad hire for months. Don't let a broken process fail someone the selection got right.

Hiring a great salesperson is one of the highest-leverage decisions you can make as a business owner. It's also one of the easiest to rush, rationalize, and get wrong. Not because the process is complicated, but because the person sitting across from you interviewed well and that was enough to talk yourself into it.

 

The process in this playbook isn't perfect. No process is. But it's repeatable, and repeatable beats inspired on a bad day every single time. Build the profile. Filter with the posting. Screen fast. Interview for coachability. Check references properly. Make a clean offer. Build a real onboarding. Do that consistently and you will get better hires over time. Not perfect ones. Better ones. That's the whole game.

Ready to get the next hire right?

Most owners find one or two spots in this process where they realise they've been winging it. If you want to talk through what a repeatable hiring process looks like for your business, book a call. No pitch. Just a straight conversation.

Book a call with Mark