In most interview situations there’s often an odd, sometimes disturbing imbalance, and it boils down to one word: power. Who has it, who doesn’t. Typically it’s the interviewer who has more power, because they’re the ones deciding who should get the job and who shouldn’t. On the flip side, a candidate who is confident he or she is the best person for the job — and has multiple offers to back up that confidence — may also have that power, resulting in them being nonchalant, cavalier, or even arrogant during the interview.
If one or both parties are focused only on ego, this power dynamic reduces something that should be a very human experience — two people connecting and talking about working together, being part of something larger than just themselves — into one without humanity. I believe this is a problem, especially when hiring a sales force, because “the interview” should be an emotional contract: One that governs long-lasting expectations and outcomes for both people during the lifetime of their employment at the company (and even beyond).
The power dynamic is further exacerbated in sales recruiting, because sales for too long had an unnecessary machismo about it, and salespeople can be so good at what they do, that they can snow the interviewer (it’s their job to sell after all). And if it’s a person with a sales background or passion for sales conducting the interview, then both parties often end up having a bullshit dialogue. They’re just sitting around swapping stories or measuring each other up without really using that conversation to figure out job fit beyond that immediate chemistry.
In all of these sales interviewing scenarios, no one wins. And it happens all the time. Sales reps will often quit within weeks or months of being hired, the company loses valuable sales revenue, and the lack of relevant data in interviews makes everyone optimize for the short vs. long term. Plus, it’s disheartening and demoralizing!
So here are some thoughts for how to make sales interviewing and recruiting legendary…
“She’s really strong, she’s great. You’re gonna love her.” That’s how most conversations about interviewing a candidate start, especially if you’re working with a recruiter. But who cares if I love her if she can’t blow out her numbers! What I want to know is, does the candidate’s experience match what the company needs? Is he or she able to sell the product? And can they sell it at the frequency and average deal size we need?
How can I trust that they have not managed to quarters, and are representing a story that sounds good, but actually doesn’t add up? All sales reps can cherry-pick and make their many deals sound very impressive, and you will not be able to keep them straight in your head or determine whether that actually makes sense or the person just got lucky a couple of years.
But you won’t get answers to these questions, because most interviews start with descriptive attributes … not data. Which is why I believe in beginning with a killer spreadsheet instead.
Before the interview, have recruiting (or you can) ask the candidate to submit their W2 and fill it in with information that foots to their W2 — the previous years payroll — including commission in the last X-years they’ve been a sales rep. Put that data together by year and preferably quarters and then calculate numbers of deals done. Then let the spreadsheet show vs. tell their average and median deal size. You will find it often paints a different picture than the one people highlighted on the outside. It’s like an x-ray: Immediately, a pattern — is this a consistent killer performer or a lucky puncher? — emerges around their performance, which helps determine their likelihood of success in your particular business and its dynamics.
Why not just ask them for this number instead of making them go through your spreadsheet-calculation exercise? Because people, and especially salespeople, will tell you just what you want to hear. I am not saying they’re lying! It’s just that most people end up remembering the best or most salient — but not necessarily the most representative — information. Or, they will share average deal size, which is not as interesting as the median, the actual range of how many deals they did, and deal-flow distribution over time.
Whether you’re hiring a sales force for small business, large business, or even working with resellers, you need to know this data explicitly. It will transform the conversation. This isn’t a temporary interview “trick” question — these numbers can be life or death for a salesperson within the organization if you can’t tell whether their deal size is based on many small deals or a few big deals.
For some products/markets, you will need somebody who does high volume, who closes five deals a day, worth $1-2K. For other products/markets, you will need someone who does one deal a year — but that’s okay since it’s a $20-30 million total contract value deal. We had both deal sizes at SuccessFactors, through our many different types of sales forces, and you need very different experience for each; the skills have almost no overlap. In companies that are going to make it big you will need both of these types of dealmakers, and you need to find out how to figure that out before it’s too late.
Many interviews in Silicon Valley end up being a bunch of self-promotional, silly trick questions that may get you into Mensa but don’t indicate much else. Or, they’re just full of hot air … and when markets are as hot as they are now, everyone seems desperate to hire quickly, while overlooking the basics.
But rushing to hire 10 sales reps — at the expense of building something that will last — will come back to haunt you later. I, too, have been guilty of allowing this, because surely it’s better to have “bad” breadth than no breadth at all, right?
The worst outcome for a company, and for a candidate, occurs when either party oversells. This is extremely difficult to be disciplined about, but it makes a critical difference in how robust and competitive a company you are going to build.
When the company oversells, the newly hired candidate will be 1-2 days into the job before they realize they were snowed. And then if they stay — which many do because of fear of embarrassment, joining an old team, loss of vesting-hurdle, and upside (“company’s growing everyone wants to be here”) — you won’t have the right person in your company. You need all hands on deck. So why over-sell? Most companies will say it’s to beat the competition. But here’s the thing: You’re not really beating the competition when you have people who shouldn’t be in your company.
When the candidate oversells, it will catch up to them in 1-2 weeks, at which point he or she will at best be marginalized, and at worst be fired 3-4 weeks after landing the job. Either way, it’s hard to recover from the unnecessary stigma this carries. It’s arguably worse for that new hire than the company because they: 1) ended up taking a dent in their resume; 2) have to deal with the emotional vacuum created by promising something and not being able to live up to it; 3) now need to explain what happened to future references and constituents (family friends, customers that they bailed out on, trusted people they hired or brought to the company); and 4) may have a harder time getting the next job.
But when you begin the interview with data, as described earlier, the bullshit interview suddenly turns into a richer, more grounded conversation. Especially if that candidate has filled out the spreadsheet in advance, you can go over the greetings and basics in the first 5 minutes and now have 55 minutes left for a much richer, more grounded conversation. That conversation ends up being much more human, rewarding in the long-term not just short term, and releases all types of interesting avenues that both parties are not used to discussing. This is because in their previous interviews, most salespeople have been so busy coming up with impressive numbers for the interviewee, and the interviewers meanwhile have been too busy building a faulty model in their head.
The killer spreadsheet approach frees up this energy and mind space. Furthermore, if you’re serious about including your sales force — really making them important strategic as well as tactical contributors to the company — this approach leaves sales reps feeling motivated and gratified whereas in previous interviews they would have left feeling there was something missing.
What if some people aren’t comfortable filling out the spreadsheet? Or they feel it’s above them (“I am a rockstar senior sales executive, why do I need to belittle myself by filling out all these forms”)? My answer: No need to apply, then. It makes me chuckle to hear that type of response, or be reminded of how some candidates bailed already at this stage. Bullet dodged.
The winning candidates will share their data with pride, and learn to speak from that place of transparency. The best part is that for a seemingly data-driven conversation, both parties end up getting to build a much stronger emotional connection throughout the course of the interview because they can focus on really getting to know each other. Data helps put the humanity back into the interview.
If you want to build a killer — not just a good-enough sales force — then I highly recommend that CEOs/ hiring VPs use a dedicated sales recruiting agency or specialized sales recruiter other than the one handling the other searches. The reason for this is that recruiting and hiring for sales is different, because salespeople are a different breed: Recruiting them takes a completely different language, a different pace, a different mindset.
While an engineer might have questions about the architecture, coding challenges, or engineering culture, and will want someone who can speak that vernacular with credibility, the topmost thing a salesperson wants to know is, “Am I going to have a pipeline? Will my territory be and stay big enough for me to make a killing?”
Of course a good generalist recruiter can learn to anticipate, respond, and solicit the right answers to these questions, but it’s not going to come off as convincing if the recruiters are constantly context switching. Since the best salespeople are setting themselves up for a pipeline, they will probe for related information and same truths 20 different ways. I really admire how rock star sales people do research on a company and find out what’s going on, and think sales-side analysts on Wall Street could learn a lot from them.
How large is the market, and the “territory” being carved out within that? Who else is there?
Are there customers you’ve already successfully sold this product to?
How quickly did the last 3 reps get to quota?
How many sales reps within the company are on 100% quota?
How many reps didn’t make it? Why?
How many of the sales reps hired are still there?
How are renewals converting in the last 10 deals sold?
Are the reps selling the same type of product?
How many price concessions have had to be given to meet quota?
The really aspirational, motivated sales reps will go even further: Is the product having an impact? What’s the runway for the product? And so on.
No matter how smart your developer-recruiter is, they just won’t be able to credibly answer these questions once the basics are addressed. The best sales reps can out-gun the CFO; heck, they could have been CFO, but deliberately chose sales. So any answers without the ring of authenticity or experience will raise red flags. You cannot afford to have a recruiter that doesn’t “speak sales”, no matter how intelligent, since they will lose those rockstar candidates for you.
A dedicated sales recruiter will handle all of that, and help you build a high-producing sales team. Of course, it depends on how big the company is and how quickly it’s scaling, but I would focus sooner than later on getting or hiring such a recruiter if you have some scale. To not escape the question of when to start: It’s not impossible to imagine a sales hire being your third employee. What?! Are you crazy, why would I do that when we could hire another engineer instead? But if you’re serious about building a great company you can’t start early enough with the infrastructure that will get you there.
And that doesn’t get the CEO and other co-founders off the hook, as they will always be the best salespeople the company will ever have. In fact, I personally do not believe in investing in companies where the CEO and founders — no matter how technical — are not comfortable selling.
One question I’m often asked is whether the CEO should really participate in interviewing new sales hires. It can only last you so long: When I was at SuccessFactors, I think I lasted until the first 800 or so hires, which meant maybe 6000 interviews (and the last many interviews were very short, so I’m not entirely sure it did much good). It’s true that candidates are exceptionally motivated to interview with the founder even if it’s short, and yes, it does allow you to check for culture.
But I think a better way to approach a more comprehensive and scalable recruiting process is to directly link it to onboarding. Rather than overselling, you’re better served holding your ground, hiring competitive recruiting, and then adding a dedicated onboarding function — one that, ideally, has content, training, and testing created by sales, engineering, professional services and customer support, and founders/cofounders.
Build your company’s “sales school” sooner rather than later. It’s the only way to scale.
No matter what the urgency is, no matter what tricks you have up your sleeve, no matter how strong your network, the reality is that it takes time to build a sales force.
The process for hiring should therefore borrow from the principles of building a sales pipeline itself. For example, just as salespeople think they have more potential sales than they actually do, hiring managers think they have more candidates than they actually do. The only way to assess the actual pipeline of candidates is to go through and rank and grade each level of the sourcing pipeline and estimate probabilities of closing the deal — just as you would for assessing a pipeline of sales (e.g., “one has contracts, one hasn’t gone through IT review”, etc.). It took me a long time before I understood the value of “sourcers” in sales recruiting, but it’s not dissimilar from having a SDR (Sales Development Representative) team for a sales force.
Just as you can’t wake up one day and decide you’re going to sell $20-million of product, you can’t just decide, “Okay, I’m now ready to hire 10 salespeople.” Your best candidates will be working someplace else, and won’t be ready to leave right away. This is why I advise companies to start building their pipeline of candidates well before they are even ready to hire a sales force. It can be as simple as hosting networking cocktail parties (salespeople are social animals who don’t find such interactions as draining as others might) or as intimate as hosting special “customer pocket” meetings where promising sales rep candidates can speak to actual customers and prospects. It may seem weird to have so many people from different companies in the room together, but works magically when done well. Frankly, inviting sales candidates to the field is one of the best ways to convince them of real interest in the product. And study them in the wild!
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Bottom line: You want reps that will stay for 10 years, not 2. If there’s one message I hope founders, CEOs, VPs, Directors, recruiters, job candidates, or anyone else reading this carries away from this piece, it’s that getting the best sales reps isn’t about getting through an interview. The power, lies, and bullshit dynamics of interviews lead people into making the wrong long-term choices, and unfortunately they are choices that don’t just affect those two people (interviewer and interviewee) — they are choices that can blow up all the constituents in a sales organization, let alone the company.
Data doesn’t just help you make better decisions in sales interviews — it cuts right through the bullshit. It helps both the interviewer and interviewee immediately get on the same page. And it moves people away from fronting with each other or playing the what-or-who-you-know game to having a real conversation instead.
One of the things I am most proud of is that a year into the sales of SuccessFactors — a company that had existed for over a decade by then — the cloud sales team we built was still mostly intact. Yet it was one of the highest-performing sales teams at the time, so they were constantly being hounded by recruiters. I believe it’s because we’d taken the time to include them in the company’s future and keep them motivated. But it really began with how we hired them: “The interview” was the first level-setting baseline, thanks to the type of guidelines shared here.
This article originally appeared in Forbes.