How do I hire a good executive for a role I’ve never done myself?

Rocks in your pockets and lead boots on your feet in a river; you go straight down.

Remember, even Michael Phelps would sink in shoes like that. That’s from one of Lil Wayne’s best, on a song called Ice Cream.

The biggest gap between functional management and general management is that GM’s have to hire and motivate people who are better at their jobs than the GM would be. Probably no CEO has ever run HR, Engineering, Sales, Marketing, Finance and Legal.

So how do you hire great people for a job you have never done?

Knowing What You Want

The first step is the most important, and often skipped. Knowing what you want is the hard part. This is how Tony Robbins used to put it: if you are not crystal clear on your goal, you are very unlikely to get it. But how can you know what you want if you’ve never done the job?

Start by admitting that you have never done the job, so you do not know much about it. Interviewing is the obvious place to start. But it is very dangerous to rely on interviews alone. Interviews are open to two traps.

If the CEO hasn’t prepared, AND the board hasn’t prepared, how clear will the hiring criteria be? How can you trust the result?

The first trap is hiring an idealized stereotype. One mistake is to hire the wrong person for the company and time. The person who was the greatest sales manager at Oracle in 2010 would probably have failed in 1989. Apple’s VP Engineering could make a lousy match at FourSquare. And that mistake is just one. An experienced interviewer knows what they are looking for, and they may be chasing some ideal that has little to do with what you need now. Worse yet, several interviewers may be chasing different ideals.

The second trap is hiring for lack of flaws, rather than for strengths. Everyone has huge flaws. YOU have huge flaws. So it is easy to slide into hiring for lack of bad qualities instead of hiring great people. That leads to interviewing for pleasantness instead of real-world strengths. What you want to find are world-class strengths in some areas that are most important to your company, right now.

The best way to get to know what you want is to do the job yourself for a while. Call the meetings. Have the 1:1s. Set the objectives. This will be especially uncomfortable if you are nervous about the role. But that is exactly why to do it. Not only will you learn the job, you will understand what you do not know.

Also, if you know an experienced sales leader, you can borrow their experience. Ask what a great sales leader does, what skills are critical for the role? Then go look for people with some of those strengths, not all of them. Even better, have them help you interview.

If you are not sure what you want from the new hire, even the smartest, most energetic sales leader might fail. What should they do in their first 30 days? Why would they want to join? Will they have 10 open reqs the day they walk in? Or 1?

The Strengths the Hire Must Have

Now turn this all into a process to find, select and keep the right person.

Write down the strengths the hire must have.

• Is the candidate world-class in running the function?
• Are they an excellent operator?
• Is the candidate a contributor to strategy? They are smart, and they can talk to other leaders and the CEO about the business strategy as a whole.
• Can they be influential with the team? Let’s not say “will they be liked.” They don’t have to be liked, they have to be able to get things done. Which would you rather have, a manager who gets great performance out of his teams but is despised? Or a manager who everyone loves, but the teams do not execute well?

So, those are the four areas. And they aren’t all equal. For the head of Engineering, or Sales, being an operator is more important than it typically is for the head of Marketing or the CFO.

Now, you need a set of questions, at least one for each criterion. Getting the questions right is one of the single most valuable exercises in the hiring process, because it forces you to define exactly what you want, and why you want it.

For a head of enterprise sales:

• Give her an honest (and gentle) critique of the company, is she smart enough to give you honest feedback and improve your plan?
• Is she smooth and articulate in describing the strengths of her current company’s products and market?
• How does she talk about your product lines and market - does she sound like she has a strong opinion and point of view, or is she generic?
• Does she have some ideas on how to approach the business?
• Can she hire great salespeople?
• What does her ideal candidate look like?
• Tell me about someone you should not have hired, and how that affected your team and what you learned from that.
• Where does she find talent?
• How much time did she devote to recruiting?
• How does her interview test for those qualities?
• Would her team follow her?
• Would you pass her interview?
• Can she hire sales managers?
• Does she have a talent spec to define what a great manager would be?
• How does she test for the qualities of the talent spec?
• Is the sales process systematic?
• How would you train sales reps to differentiate between “business” and “technical” objections, and then handle each one?
• Has she installed sales success tools like lockout documents, POC contracts, standard pricing, standard workflows for demos and benchmarks?
• And, does she know how to use them, and teach the skills?
• Can she train it, and does she enforce it?
• Does she enforce CRM system rigor, discipline, cadence and training?
• How does she train a new hire?
• What is the mix of process training versus just selling the product?
• What do the training materials look like?
• How good is she at turning around a failing rep, and by what criteria?
• Is there a rating system for the reps to evaluate them by quality, not just by sales results?
• Can she explain, clearly and helpfully, the difference between transactional and enterprise sales reps?
• Can she design comp plans, with accelerators, and spiffs?
• Is she able to close a big deal herself?
• Has she made deals bigger and closed them faster? Can her team back up what she says about her closing, her strategy and tactics?
• Talk to customers on references, and confirm her abilities.
• Does she understand marketing and its three main roles: brand versus lead gen versus sales enablement, without prompting?
• Does she understand all aspects of distribution channels, the conflicts inherent, and how to manage the incentives and internal conflict resolution?
• Is she intense?
• Is your rep in Wisconsin making calls starting at 5 am or going to lunch at noon?
• Does she have international experience?
• How connected is she in the industry? Does she know the top players at your competitors, your recent deals, your org chart?
• What strengths does she look for in a direct report?
• How does she find those strengths in an interview?
• How does she train them in the real world?
• How does she evaluate a direct report in a performance review?
• How does she get the information she needs to decide?
• What is her decision process?
• What is the meeting format? Is there an agenda?
• Are all commitments captured, and are results captured and measured?
• How much time has she spent learning about the org, customers and market?
• How did she design her key management processes? Interviewing, evaluating performance, onboard process, strategic planning process.
• What were leading and lagging metrics for the prior team?
• What are the 2 sides to each leading indicator, e.g. speed vs accuracy, impact vs ease of execution?
• How do side effects get identified?
• How were these designed, versus just stumbled upon?
• What is the structure of her org?
• What are the pros and cons of that structure?
• Why did she pick that design?
• What are the strengths she values, and why are those most important?
• Are there any conflicts built into that structure, and how do you resolve those conflicts?
• Territory changes for a high performer? By what process?
• How does she promote and fire?
• What does she do when her best performer behaves badly? What does she do if it is not fixed?
• Is she a systematic thinker, or does she operate ad hoc?
• Would you want to work for her?
• Does she play straight with you, or is she a spin-meister?
• Does she ask sharp, unscripted questions that make you think hard?
• Does she adapt easily to a variety of interviewers?
• Is she very articulate?
• Does her research on the company, industry and competition seem thorough?

Interview Team

The next thing to do is build the interview team. There are only two questions that determine who should be on the team.

First, who can best judge whether the candidate meets your criteria? These could be people inside the company or outside it.

Second, who needs to support this person once you hire them? You can’t hire an excellent CMO if they will be sandbagged. Surfacing any reservations before the hire will protect the hiring.

The interviewing team can be two different groups. One group picks a set of finalists for their world-class talents. Another group who should be on the team are the people that the new hire would need to work with every day. This second group should wait to interview until there are finalists.

For an important job like this, the easiest way to get great answers is to assign questions by people’s area of expertise, and make sure each interviewer knows what a great answer will sound like.

After every interview, debrief with each interviewer. Their impressions can point out things you missed, and your impressions are valuable to them. This builds teamwork on the hiring team. Over time this leads to everyone learning more about the criteria, and having sharper questioning.

Your job now as CEO, before you hire the candidate, is to check references. Do it yourself. Why is this so important? Because you have defined the person’s strengths, or weaknesses, that you want, and you need to confirm that the references agree with you. Also, you can learn a lot by talking to people yourself. And do several “backdoor” checks, by people who know the candidate but were not given by them. Backdoor references are important because they are unbiased, but don’t skip front door references. Front door references won’t paint the candidate in a negative light, but they are still valuable because they will show whether there is a good fit between the new hire and the role.

The final hiring decision is not a consensus. It’s the CEO’s call. Consensus can drift into interviewing for lack of weakness instead of world-class strengths. It’s lonely to decide, because you are the only person to see all the criteria and all the feedback. But that’s one of the most important functions of a CEO, and there is no substitute for it.