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Hiring Your Dream Team

Chris Winn
Creative Market

As a first-time engineering manager in 2014, I inherited not only a team of people but a management and hiring philosophy. A lack of trust in people to contribute and do great things led to low morale, lack of technical innovation and hurt productivity. In this talk I show hiring managers how to consistently bring in great talent and build the team they've always dreamed of leading.

We're all here to listen to that song. So hi, I'm Chris. When I'm CTO at creative market my talk today is always wear a light shirt so people can see your wrinkles. I'm gonna go with the. Other talk if we stay on my slide can go back. Okay. So I'm going to talk today about how to hire your dream team.

I joined creative market about five years ago and I showed up to a team that was pretty broken. We had old code, we had old frameworks, we had tech debt. My team is here. We don't have any tech debt anymore right now, no way. But we had low morale too. It was a really, it was a team that was hurting.

And one of the reasons we had low morale is because we had a top down management philosophy. It was a management philosophy that didn't trust engineers to do the engineering things like make decisions and. It didn't feel right to me, it didn't feel like a fit for the type of manager that I am. I'm a bottom up manager and I didn't realize it at the time.

But one of the things that was happening was I was starting to form my own opinion about what my team should look when you get yeah. The promotion or you joined the company and you're a first time manager. You think you are going to inherit a team. And you do, you inherit a team, but you inherit something else too.

You end up inheriting someone else's management philosophy. And because of that, you end up inheriting someone else's hiring philosophy too. As a manager, you're going to be graded by the productivity of your team. And I have fantastic lead bad news for you, which is. That really important, critical career defining thing that you are solely responsible before?

No. One's going to tell you how to do it and no, one's going to tell you how to do it really well, but I have good news for you. The good news is I have seen some things and I have also screwed up a lot of stuff over the years. So what I'm going to give you today is a framework. Now hiring is different.

At every company it's different at every team. It is even different from hiring manager to hiring manager. So this is something you're going to take home and you're going to make it your own. But if you do it right, you can end up with a phenomenal team. Cause I think so step one, know your management philosophy.

Ask yourself. What do I value? You know, you're paid to have opinions. You are paid to express those opinions. So think about yourself, honestly, as a human being, what do you value? You know, you might value people who are on time. You might value people who are scrappy achievers or whatever. In the long game to be a great manager, you've got to individualize and you've got to work with a lot of different personalities, but if you're new to this and you're new to team building, you get to be a little selfish one time and just think about what's going to work, or what's going to work for your team.

Number two. And as a quick aside, by the way half of this presentation was designed by our design team and the other half was done by me. And I'm not going to tell you, which is which. Aligned to what your company needs, why

you still don't know

what type of engineering team does my company need. You've got to be able to draw a line from what your company needs to, what your team is going to do. You know, are you the three person startup? Well, you don't have any engineering managers. Nevermind. Are you the, the high growth startup that needs people who are just gonna kick ass all day?

Do you have a product that has special compliance needs? You've got to think about what kind of skill set is going to fit within my company. And you also want to think about stakeholders who interacts with my team, who interfaces with my team could be a product manager. It could be a set of designers.

How are they going to grade your team? If they're going to work with you. So think about these things, build your pitch. It's a competitive market. Your job is to get talent through the door, but you have to have a really honest pitch. You've got to paint a really accurate picture of what it looks like to work at your company.

That is also compelling. If your pitch is not honest, you're going to get really laser sharp at bringing in all the wrong people onto your team. And I think every great pitch has a narrative arc. That's how my brain is wired. Do this your way. But I always have a kind of a three-act structure to my pitches.

Our company has an incredible challenge. You are uniquely qualified to help us meet the challenge and three, we can't do it without you got us on the offer letter, pick your hiring tools. Hiring is all about top of funnel. So that you can comparison shop. And especially if you are new as a hiring manager, you need to talk to a lot of people to start firming up your opinions about what's feeling right tools also help you stay organized and organized matters for two big reasons.

Number one, being organized is going to define what the candidate experience is like, and that will speak to your reputation and your company's reputation. Being organized also means something else does something else, which is it's going to help you not lose the person that you actually really liked, but you lost sight of them.

Cause everything's like every day. But you remember too, that your process is their first experience with your company. So it really does matter. And the last thing I just wanted to squeeze in here, email is not an option you are allowed to pick. Even if you're hiring one person, email inbox is not a good organizing tool for hiring squeakiest age.

So number five clearly define your role, know what you need. Again, have an opinion about what you're looking for. You can cast a wide net and you've gotta be really careful with job descriptions. You don't want people's self filtering them selves out, but you still have to know what does success look like for this hire?

And another thing I always tell people at the beginning of the process, no. Why you would say no. Why would you walk away from someone? What are the table stakes for a new hire and do this at the beginning because. You will end up later in the process, investing so much time in people, your brain will find, find ways to ignore yellow.

Red flags you'll want to move forward. Maybe it's because of external pressure. You've got to make that higher. Maybe it's because of internal pressure. I'm a new manager. I want to do a really good job. My job is to hire. So I need to hire, go in knowing why you would say yes and why, why you would say no.

Build an interview. I talk about hiring a lot to people. It's amazing people forget to think about this step because it's literally what it is. We're interviewing people think strategically about the questions that you're going to ask. What are you asking? Why are you asking it? What's the intention behind it?

What are you trying to pull out of the person you're talking to? I'll give you some examples of what works and what doesn't work. Hey, are you a good planner? Yeah. I, I like to think of myself as a good planner. What did I learn from asking that? Nothing. I didn't learn anything from it. There's a lot of different strategies to like get to the thing from someone.

But a couple that I use a lot, I call it, make them choose, make them demonstrate. Here's an example of make them choose. Hey, when you're working on a project, what do you love more the building or the planning part or the building part? They're going to make a choice, then ask why dig into it a little bit.

Another example, make them demonstrate. Tell me about a time you had a crazy complicated project. How'd you approach it? Them talking about it. You'll learn so much if you listen and you get them speaking. And remember another thing, if you end up hiring that person, that interview, that was your first one-on-one with a new direct report.

This happened to me one time I was interviewing someone and I fell a little bit off of my own interview questions and she, and I ended up having this really fantastic conversation about values and about how, you know, how you build a team and what the company's about it. It was an interview that went on for an hour and a half, and I ended up hiring her.

And I noticed something that when we were in our first one-on-one for the first time, it was like we had worked together for years because my relationship with her started back in that interview process. And she got a sense of my values and we had a trust already built up. So even if you end up saying no to 90% of the people, you talk to always treat them with respect and always approach it from your building, the relationship.

Create a hiring panel. You want a lot of diverse voices. You want a complete view of a candidate. You want everyone approaching their questions from a unique perspective. It's okay. If some of the questions overlap a little bit, it's actually interesting to see a candidate answer a question multiple times.

But let them know that to be on that panel is a huge responsibility because they're going to be representing your company externally to the outside world. So make sure you say that and have them write their questions down, be the editor, you control your hiring process. And it's very likely that they're not going to prior experience hiring and they didn't come to calibrate.

So. You know, be the editor, give them feedback, direct feedback. Hey, let me talk to you about this question. What are you trying to get out of this question? Could this be more direct? Is there a different way to ask this, get everything sorted at the beginning, you're going to touch it one time. It takes some work, but once it's done, it's done.

Run a skills assessment. Number eight code challenges in our industry are super broken and there's actually a lot of really interesting things happening. But I haven't seen the silver bullet yet. My personal high level is make it mirror real work as much as possible. What does it actually look like to do work at your company?

And how big is the gap between that and the code challenge. You know, you want to give them a chance to do their best work, but think about all the disadvantages a candidate has with a hiring process or a code challenge. Well, they don't get any time to do it. Oh. And by the way, if you don't do it well, you lose your job, meaning you don't get the job.

It's really high pressure stuff. And. What are all the other things missing that they would have fewer if they were at your company? I think about my company. Well, they have engineering management, they have tech leads and we have a definition for that. We we have product managers, cross functional teams, designers, collaboration, support tools, onboarding, it's crazy.

This stuff. They're not going to have doing your code challenge. So level the playing field a bit. Another thing that I find tremendous value in is remembering that a skills assessment is an opportunity to see some other things too. It's not just about their hard skills, their requirement's checking those boxes.

You're again, you're building a relationship. You're going to learn other stuff. How do they take feedback? If I poke and prod and I add, ask a question about their process or their work, they respond to it. And there's different, right. Answers to that, you know, they might say, thanks. I appreciate hearing that.

Let me explain to you my thought process and what I was thinking at the time. I love that because I might be wrong. I might learn something from them. That's the kind of team I want. If they take it personally. If they shut down, if they're not used to getting feedback, that's something we've got to work out.

That's a flag. That's not going to work for the type of team that I built,

checking references. I heavily biased toward talking to managers, but whoever you talk to and you should talk to the people around them at their team, make it easy for them. Create a safe space for them to give candid feedback. You know, I, especially with managers, a lot of the time I will sort of make it manager to manager a little bit, and it's not dishonest.

If I've gotten to a reference check, there's a really good chance that I am going to hire this person. And I might say something like, Hey, really excited about her. I think we're going to move forward. Help me understand how to support her. What's a time when she struggled a bit failed, got frustrated.

Tell me how to be a good manager to this person. The worst case scenario is you'll stumble upon a lot of stuff that you didn't learn from the rest of the interview process, best case scenario. You're just going to learn a lot in general and be a better manager and be able to support that person. So references are going to provide a lot of really, really good information for you and spend time with them too.

There's obvious things too. If, you know, people are always going to be in a position. If, especially if it's a good candidate, they're going to want to go up to bat for someone they're gonna want to pitch a little, they're gonna want to support someone. It doesn't mean, but it doesn't mean they are being biased, but it doesn't mean it's a bad thing.

It just means they really want to support this person. Versus another time I remember reaching out to a reference, I was provided, I got an email back from the manager and it said, yes, I can confirm their employment during this time period. I was like, well, that's good.

So you got to watch out for that stuff, but it's really good. Talk to a lot of people and do talk to the people on their team to remember that, you know, and again, you're going to meet all kinds of people, but if they're ICS, you really want to go out of your way to make it that safe space. Because they're not always going to be tuned to give direct feedback, especially if they think there's something on the line for a person that they knew, number 10, how to close the deal.

You're hiring process should feel like it has a consistent cadence to it. You know, typically our hiring process is two weeks. If you're a director and now you're talking to a lot of other people, it can be a longer process. There might be travel involved. But you want to make sure that there's a really consistent cadence to it.

You want to make sure that you know what the next step is that you communicate what the next step is and when it's going to happen. And then you want to follow through and make sure that that actually is what happened when you said it was going to happen. Give the candidate are really great experience, but toward the end, The momentum should pick up a little bit.

It should start getting a little faster, especially once you have sort of turned your key and you, yeah, you are sure we are hiring this person. You want to create some momentum around it. You want them excited. Remember they will be talking to other people. One of the things that will help you win too with a great hiring process is that's going to be in their decision set too.

If they're considering other companies and one company, even if that company. Pays better or has the better thing or the cooler office or whatever. One of the things they're experiencing is you and the people on the team and the process I've literally had a candidate who told me sometime later they had another job offer from a company we're 50 people at creative market.

They had a job offer from a, a pretty name brand San Francisco company that. You know, was a great offer for them. One of their, one of the reasons they decided to go with us is because we had a phenomenal candidate experience. And every time they talked to someone at the company, they really got a sense of what we were about.

Sure. We want to get that offer letter signed and you know, being new to this too, you got to cut yourself. Some slack hiring is slow. And it's hard and it's frustrating. And then it's awesome. Cause you found someone and they signed an offer letter and they're joining in three weeks and oh my God, they're going to change your team.

Right. And then it's slow and then it's hard. And then it's frustrating and it just keeps going the way it is. Don't worry about it. Give yourself a break. Hiring is the thing just like people management. You're not allowed to screw it up at least not for very long. So you got to learn fast, you have to care about it, but developing your hiring process is also a fantastic way to explore your own management philosophy.

To explore your values. Your values are going to be all over your hiring process. It's also going to help you think really deeply about your own team. If I have a strong opinion about what success looks like, and maybe I inherited a team and I have people behind me that don't match that vision, what does that mean?

Can I get them there? How do I get them there? If I can't get them there? What does that mean? It's really a great self exploration process, but if you do it right. And it is going to be hard and you are going to make mistakes, but if you do it right, you will end up hiring your dream team. Thank you.

About Calibrate—

Founded in 2015, Calibrate is a yearly conference for new engineering managers hosted by seasoned engineering managers. The experience level of the speakers ranges from newcomers all the way through senior engineering leaders with over twenty years of experience in the field. Each speaker is greatly concerned about the craft of engineering management. Organized and hosted by Sharethrough, it was conducted yearly in September, from 2015-2019 in San Francisco, California.

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