Startups | 8 min read

How to make sure you’re hiring the right people

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Recruiting at a startup is a high stakes game. Attract and hire bright, ambitious people who are excited by your mission and it’s like giving your company a new superpower.

But get it wrong and you can easily set yourself back a couple of quarters as you start the search all over again.

Having personally recruited 200 or so individuals and built teams that have hired thousands, here’s five things I’ve learned that help ensure you’re recruiting the right people for your startup.

1. Intellectual curiosity and communication are key

Why does this matter?
In the early stages of a startup, you can’t be successful if you’re heads down living in an isolated world. Those who want to dig in and understand the larger environment, and can communicate well cross-functionally, are better equipped to grow with the company.

Starting from scratch or rebooting a search is a better decision than hiring the wrong person.

How do you do that?
The questions candidates ask are a great way for interviewers to measure intellectual curiosity and communication skills.

  • Is the candidate interested in the big picture?
  • Are they trying to better understand how the business works and what the organization values?
  • Do they want to explore how their position impacts the business?

If so, these are all signs that this person is thinking broadly, communicating well, and demonstrating that sense of curiosity.

Another way to measure these skills is to provide a candidate with an exercise. After they complete it talk through the process with him or her. Ask what they got out of it, what was difficult, what they enjoyed. At the most basic level, the candidate should be able to walk through his or her thought process in a simple and organized way. To measure intellectual curiosity, ask the candidate why he or she found it interesting and how they might apply the skills necessary to impact the business. How they answer will exhibit whether they can think big picture.

2. Don’t oversell. Sometimes a decline is a win.

Why does this matter?
As employers we have to get past the idea of “winning” in the traditional close-the-deal sense. Our goal is to provide somebody with a positive and honest experience. Self-selection is a beautiful thing. If we are open and honest about the position and the state of the company but the candidates does not want to come on board, we should consider that outcome a win.

How do you do that?
Our recruitment team’s goal is not to make Intercom everything to everyone. Being open and honest about where the organization is today, but marrying that with optimism for the future, allows us to be aspirational yet realistic.

For example, many candidates ask us about career development. Sending the message that we have a highly defined career ladder for every position and a guaranteed promotion path for each job might close the deal for some candidates but backfire long term.

We choose instead to explain to candidates that we are still in a phase where folks, in most cases, have to forge their own path and that possibilities, while endless, aren’t clearly defined. This approach allows us to identify people who can handle, and even get excited by, a degree of ambiguity. It also ensures expectations are aligned if they choose to join us.

3. Zoom out when selling the vision

Why does this matter?
Products, packaging, and statistics change. It can be a mistake to get caught up in the technicalities and functionalities of specific products when pitching an opportunity to a candidate. Overselling the stage of a company (e.g. placing a lot of emphasis on hyper-growth) or focusing on a possible exit strategy can be a mistake as well – the growth and exit strategy of a company can change quickly. Keeping the pitch high level and focusing on what the company believes in and values is a better way to attract candidates who are going to remain engaged as things constantly change.

How do you do that?

When I pitch Intercom, I focus on customer communication more generally. For folks who have worked at a company where they build something, the idea that you can better engage with your customers and give them what they need in a simple and pleasant way-is super appealing.

When that doesn’t resonate, I connect the candidate to the experience we are attempting to improve for the consumer. Every single person I talk to has has some negative experience as a customer and has tried, often unsuccessfully, to engage with a business when they need help. Our mission resonates with these folks immediately. It’s nearly impossible to not want to get behind a product that’s going to empower companies to do right by the people who use their products.

4. Don’t let your hiring managers get desperate

Keeping the bar high is
your best recruitment tool

Why does this matter?
Although not ideal, I advise scaling back a project or delaying a deadline over rushing to hire someone and settling on the wrong person. The cost of hiring, onboarding, training, managing out a poor performer, and then starting the backfill process can take months. Often starting from scratch or rebooting a search is a better decision than hiring the wrong person.

How do you do that?
Intercom does a great job of taking the time necessary to build a product the right way the first time. If we think we built a great product but it’s not performing the way it should or resonating with customers, we’re not afraid to go back and start from scratch. We try to mirror that approach in hiring by not just rushing to get it “done”.

We align our recruiters around the goal of hiring the right person, over hiring a ton of people as quickly as possible. Your recruiters can coach hiring managers, when necessary, to take a step back and think about the long-term impact of hiring the wrong person. In the situation where you don’t have a recruiting team, the execs should be leading by example. At Intercom, it is not uncommon for C level executives to remind the whole company that they aren’t going to settle or rush to hire someone. This approach has a trickle down effect.

5. Keep the bar high

Why does this matter?
Keeping the bar high is your best recruitment tool. Great people want to work with other great people. Great people do great work that other great people want to work on! We keep the bar high by looking at each interview as an opportunity to learn something. At the most basic level, we want to interview someone and walk out saying, “That conversation was really interesting, I learned something new”.

How do you do that?
Some folks are more comfortable opening up in an interview than others. A great way to get into a meaningful discussion and properly evaluate a candidate is to create a standardized baseline exercise. The idea is to replicate a problem very similar to one the candidate would face in the job. You will often see candidates open up during these exercises. Reviewing it with them and understanding their thought process is often as important, if not more important, than the solutions they come up with.

These exercises can be particularly helpful when you are hiring for potential. For example, when we hire recruiting coordinators we have them work through hypothetical scenarios where a bunch of things go wrong at once. To evaluate how they would prioritize in real time, we ask them to walk us through what they would do. Additionally, we provide these candidates with real calendars and candidate availability and give them 15 minutes to try to put together an interview on the spot. We aren’t looking for the perfect interview panel. This exercise allows us to evaluate the candidate’s instinct, ability to remain calm under stress, ability to ask good questions and be creative, all while working under a time constraint.

Make the investment up front

Hiring the wrong people can be damaging in so many ways. There’s a financial cost. There’s a time cost. There’s an opportunity cost. It can damage morale as the rest of the team start to question your judgement.

And with a small window to capitalize on the opportunity you’re going after there’s always a temptation to “close the deal”. But putting the work in up front, with the same kind of discipline you would use to build a new product, pays off in spades down the line.


If you want to reach out to Maggie, like all good recruiters she’s pretty active on LinkedIn.

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