How to Recruit Senior Managers that Fit Your Culture

hiring series a Apr 08, 2019

There are few things more frustrating than working with someone who’s the wrong fit.

Hiring well is what defines success, but damn, it’s hard. And firing fast, after you find out things aren’t working, is even harder.

For the longest time, I searched for the magic bullet — a question, a test, a process — to predict who would work out. But even the strongest recommendations from people I trusted were hit-and-miss.

Reflecting on my Best Hires

Thinking about the people I love working with, I can’t help but smile. They are people I learn from, whom I trust, and who consistently produce fantastic work. With them, I feel more comfortable, more courageous, more inspired and more energised.

However, with people who aren’t working out I feel uncomfortable, worried, anxious, and — my least favourite emotion — underwhelmed. Over time, these relationships tend to drain me and, in the worst case, I avoided them altogether.

This got me thinking. If I could figure out the qualities of the people in the first group, could I find a way to find more people that I love working with?

Feelings are a Critical Data-Point

All the people I love to work with have one thing in common: the way they make me feel when we work together. I’m not saying that feelings are the only data point — of course, you need to hire qualified people with good references. But you have to use your emotional intelligence too.

Emotions are powerful. They tap into our brain’s pattern recognition systems. And yet gut instincts have a bad rep in business. One of the main reasons for this is that we all have a gut response to everything, even when we have no experience to draw on, so when we’re faced with novel business challenges, our gut instincts often lead us astray.

However, when it comes to working and spending time with people, we have decades of direct experience. When it comes to judging people, our intuitive brain often outperforms our rational minds. Paul Graham, YC’s founder, writes about the counter-intuitive nature of startups, but follows it up with:

Trust your instincts about people. And in fact, one of the most common mistakes young founders make is not to do that enough,”—Paul Graham

The “Important Work” Feeling

Not all feelings are equal. The first impressions you get from casual meetings and interviews aren’t very reliable. Instead, the feeling that I pay attention to is the one you get when important work is being done.

It’s a bit like dating . . . the first date might go really well — they seem positively charming! It’s only when you encounter a vulnerable situation (often while planning, travelling, or during some other project or crisis) that you realise that your expressed values aren’t aligned.

Important work is that point of vulnerability for managers and founders. So, involving important work in your recruitment process will help you take better decisions by evaluating not only the results, but also how you feel about working with the person.

I’ve had my best results from starting with projects that focus on real-work, to test the waters in a safe way. Some call it ‘freelance-to-hire’. The projects last anywhere from a few hours to a few days. It may sound like an expensive use of time and money, but trust me, it’s far less expensive than hiring the wrong people.

No Excuses

When the work is done, it’s time for some radical self-honesty. Are you feeling inspired, impressed and energised? If so, you might have found your person. But if not, if there’s a niggle, a bad impression, or a sense of ‘underwhelmed’, that’s a big red flag.

In the desire to ‘hire fast’, our minds can make excuses: ‘Well, perhaps they need some more time,’ or, ‘I can’t expect them to know everything.’ But, in my experience, these feelings and excuses rarely go away.

In fact, they often get worse. When I’m anxious, I instinctively want to jump in and micromanage — or worse still, ignore and avoid the person. Pretty soon, both sides feel frustrated. No-one wins.

Is Performance Enough?

What about people that produce fantastic results, but you still get that uncomfortable feeling? It’s easy to ignore that niggle in the name of moving forward quickly — but it’s a slippery slope. That niggle is an indicator that some cultural value isn’t aligned.

Culture fit is extremely important in a growing startup because bad apples tend to proliferate. Sometimes the smart thing to do is say ‘no’ to short-term wins in order to invest in your long-term culture.

Hiring Fast and Slow

The famous adage is ‘hire slow and fire fast’. Finding short projects for candidates, to test the waters, is a practical way to do this. And remember, it’s not only the project’s results that you have to go on . . . it’s how they make you feel.

If something doesn’t feel right, it’s time to ask the hard questions. Is this a culture fit? Are you making excuses? If so, you know what to do. After all, you’re in charge, aren’t you?

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