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At Techstars, we often hear from startup founders that hiring is one of the most challenging things to do right. We recently held an AMA on this topic (Ask Techstars: Hiring & Culture – Scaling Your Startup) with me (Sabrina McGrail, VP of People at Techstars); Emma Straight, Sr. Recruiter at Techstars; and Natalie Baumgartner, Founder & Chief Psychologist of RoundPegg, a company culture and engagement tool.

This post is the second in a series of three with Q&A excerpts from this AMA. Check it out!

How do you make remote employees feel part of the team?

Sabrina: We are actively trying to figure this out at Techstars; we are in 30 locations in 10 countries at this point so we are all over the place. When I chat with people on video calls and ask them how they are doing, I am always so grateful that they are saying they feel connected to the team. Sometimes it’s the simple things, like in the on-boarding process to always get on video calls versus calling someone over the phone. Have more tools where you can connect in real time with people. It does depend on your company and what is right for your company. I know a lot of companies use Slack heavily, (we use Slack), and we use Voxer, which is basically like a walkie talkie, but it really helps me feel connected to people on the fly at work. With time zones especially, and this is one that we have had trouble with since we are all over, before you set a meeting, make sure it is at a time when at least most people can attend. Record your meetings so you can send them out after the fact for people who weren’t able to attend. Find different ways to be considerate, it was a learning process for us and it still is every day. Take time to get feedback, especially from remote people, on what they thought of a meeting or if they feel the level of communication is where it needs to be. It’s a lot of little things stacked on top of each other.

Emma: I worked remotely for about five years for companies in the US; there were some things that really worked and some things that didn’t. The number one thing for me that really helped was that if there was any kind of company meeting, holiday party or anything like that, to get the invite to it. It really helps to feel like you are welcome at those events. Try to make sure  you have someone there as a point person to introduce you to everybody and make you feel a little more involved, while also making sure that everybody knew who you were. Those are really important things. I know there is a cost involved, but there are also cost savings with not having someone in a physical office, so that can kind of equal out in the end. Really getting together live and in person is essential, even once per year just to make that connection. I worked for a company in San Francisco and I was able to go out once a month. That helped tremendously to actually get to know people in person.

Natalie: We talk with organizations about this a lot at RoundPegg because, to your point, it is becoming more and more common that people have remote workforces. I was at an event not too long ago where the topic was around culture and disparate workforces. It is really important to not forget about your people that are remote and to really incorporate them and be mindful. It is so easy for that not to happen, not intentionally but just in the busyness of work and lives. Use culture to find out what people’s core values are to link them in. If the value is team orientation, give more opportunities to orient that person into the team. Culture is the glue that holds us together.

If a full time employee’s work doesn’t provide good ROI, or you realize that the person doesn’t fit well with the company’s culture, is simply hiring and firing legal?

Natalie: One of the things that is important to talk about when you bring someone on the team is where you see the synergies and where there might be some gaps so that the stage is set from the beginning. Culture does not have to be good or bad, it can just be a poor fit. So setting it up from the get go, such as a, “Here is where we stand, let’s just watch these things that may not work between us.” It’s just easier to have that tough conversation when it becomes really apparent that there is just not a fit – you’ve been in the conversation all the way along and so you can have that conversation on the fact that those things that you are not aligned on aren’t playing out that well. If it is handled that way, people will self select out. When it comes out of the blue is when there can be a problem, and perhaps they even feel like they are a great fit. Those separations are far more painful.

Sabrina: Those are really good points, especially setting expectations early on. It happens often where you’ll hire someone and they are great at 90% of the job description but the other 10% is something they are really going to need to work on. Setting the stage early on so that it’s part of the discussion is the key component to managing the relationship the right way. Make it a constant conversation and have regular one on ones to check in on progress on how those things are going. From the legal perspective, the US is at-will employment. Every country has different employment and labor laws, so if you are outside of the US those are things to look into. That being said, in the U.S. you can terminate someone without giving them notice or without performance discussions. It is not a best practice. From an employer and brand perspective, you want to make sure that you are doing what is right by the employee. When I have these conversations with people about performance, the best way to approach the situation is to consider what you would want if you were in that position. If you weren’t doing well or you weren’t fitting, wouldn’t you just want to at least have a direct, open discussion about the problem and try to at least feel heard throughout the process?

The goal is to make sure it is not a surprise, but it is not always perfect. Some people really feel rooted and aren’t understanding or are missing what you are saying to them. Just try to make sure you are being as direct as possible when things aren’t lining up and take a step back to see if there is anything that you or the environment is doing to make it really challenging for them. Be a little bit introspective as a manager in the process because it might be something that will come up more and more as the organization grows, so taking that step back is important as well.

Emma: I agree with all those points. Having the conversation early, setting expectations from the beginning, and also giving them a chance. Sometimes there is just a misalignment or miscommunication that they did not realize. The flip side of this is to try to invest in management training because there are so many poor managers. Either they never should have become a manager, or they just haven’t had any training to do so. That is a huge investment for a company. It is so valuable learning little tips along the way, how to communicate effectively, how to understand where someone else is coming from because they may be very different from you. RoundPegg offers the solution to learn how people work best to and almost learn their language, trying to get a midpoint between two people who may be very different.

What few things should candidates do to vet a startup before accepting a job? ex: culture, management style, mission.

Sabrina: Get an understanding of where they are at and where they come from – the history of the startup, the progress they have made, why they are there as founders, and walk into the interview with a set of questions for each person that you speak with that touches on something a little bit different to give you a good sense of the environment and what you are walking into. Questions like, what is your average work week? What is the pace like? What are communications like? More specific questions can include, how are we doing? What’s our runway? Dive into the details in the interview process and ask the same questions a few different times to different people to see if the stories align. You can also just look around the office to see who is working there too, is there any diversity there? Is it clearly just a group of guys that went to college together and are now building this thing? You have got to start somewhere so it’s not that, that is a terrible thing but if it is that way, maybe bring it up in the interview process. Just pay attention to your surroundings and how people are working together.

Natalie: If you ask an organization what their culture is like, it is important to note that we all have different understandings of what culture is and what that word even means, so maybe a better way to get more rigorous data would to be to ask them, how do you do things here? That is what we think about when we consider culture – how do you make decisions? What determines what gets prioritized? How do people communicate here? And what gets rewarded? That doesn’t mean just monetarily rewarded, but what gets encouraged and supported? If you ask about these specifically, you should be able to get a much better read on the culture. If you just ask what their culture is, you may just get answers about their off shoots of culture, answers like, we have a lot of fun here, we’re great, we love each other, we have been together forever, we have a keg, etc. These are things that come out of a culture but they are not really culture.

Emma: When you’re going into their office, really try to pay attention to everything. Look around, who’s working there? What is the vibe like? I had an interview once at a startup and one of the co-founders just kept yawning during my call interview and I was like, well this is not a good sign for so many reasons, but he’s exhausted. So I asked him what he likes about his day and it was a very lackluster answer. That was the person at the helm and running the organization, that behaviour and attitude is going to trickle down and that spoke to me. Also, ask what their retention rate is and if people are leaving very quickly because that could also be a sign. Try to talk to as many people as you can and try to get an authentic answer of what they’re liking and what they’re not liking. It’s always hard in an interview setting, but just pay attention and ask a lot of questions.

What pro-tips do you have for startups or scaling companies to best vet culture fit during the interview process?

Emma: We use RoundPegg, I think it helps. It should not be an indicator of who you should hire and who you shouldn’t hire, but it does help to assess who a person is, how they look at things and how they communicate. It also gives you an understanding of how to communicate more effectively with them. During the interview process, it is always hard because people are probably giving you the best side of themselves, so it is important to have more than one person interview them. Maybe take them outside the office setting, like go get a cup of coffee or take a walk to let them have their guard down a little bit. Also, try to ask other people that had contact with them – ask the receptionist how they acted with them. This is always important because a lot of people treat different levels of people differently. People on the interview team have to be really attentive to things they are feeling, noticing or seeing and how they are communicating via emails, how quickly they get back to you about scheduling an interview, how flexible they are about scheduling interviews, etc.

Natalie: Even if you aren’t using a piece of technology to evaluate culture and culture fit, just get clarity on what the three to five values are that are most important to you. A quick and easy way to do that is to jump on RoundPegg and make a profile for free. Print out your profile and sit down to find what the three values are that you have in common – what are the few that are most core to us as an organization? These are what you really want to be evaluating. However you gather that data, you need to understand the three to five values that are really inherent to what you are and what you want to build your company on, and then you need to be able to, in some way, figure out what is important to this individual that you are interviewing. This is difficult in the interview process because you are selling yourself. Have a list of strength based values and ask them what three they think are the most important to them and then talk about it and ask for examples. This way, you can get under the surface and gain a richer understanding of who someone really is. For example, RoundPegg’s value is being organized and it has been one of our values from the beginning and as we have grown and shifted. One of the questions that we ask is, “talk about a time when you worked in an organization where there was very little systems or processes in place and when it was a problem for you, as well as how you managed it.” That kind of behavioral interviewing question about culture can give you a lot of information.

Sabrina: What I try to do during screens (and it is a lot easier during the first screen than it is down the line) is try to understand their happy place and their unhappy place. I try to get really curious about it and use digging questions about interpersonal relationships, team dynamics, environment and pace. Who is the best manager you have had and tell me about that relationship? What is your least favorite work environment you have ever been in?

Click here to listen a replay of this AMA.

Join us for our next Ask Me Anything session with David Cohen, Co-Founder and Managing Partner at Techstars – June 23rd at 10am PT! Ask anything about startups, fundraising, accelerators, and more! REGISTER.


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Sabrina McGrail Sabrina McGrail
As Vice President of People Ops at Techstars, Sabrina is responsible for all things talent, culture and human resources across the organization. Her focus is mainly on internal talent acquisition, retention and organizational development within Techstars. Sabrina received a BA in Communications and Information Technology from UMass Amherst and is now enjoying her time living in sunny Boulder, Colorado. @sabrinamcgrail