Dear Reboot: How to Hire Smart, Plan Consciously, and Avoid Pitfalls
Designing well-thought-out recruitment, hiring, and onboarding processes.
In our Dear Reboot series, Reboot coaches aim to provide guidance on common leadership dilemmas. If you’d like to submit a question to be considered for our Dear Reboot column, email us here.
Dear Reboot,
We’re growing fast, and I’m thinking about hiring six new people in the next few weeks. We have some crucial roles to fill. How should I be thinking about hiring so that we don’t waste our time on bad hires?
Dave
Dear Dave,
Some of the biggest pitfalls we see leaders falling into are around recruiting. You would think that bad hires happen when no one else is looking. Yet, they can happen even with the best of intentions, with the candidates that look the best on paper, and with the best pre-screening in the interview process. What are the missing considerations? After supporting clients navigating challenges related to recruiting, and hiring, whether that be scaling an organization, hiring for one particular crucial role and beyond that, we’ve noticed some patterns. Here are some things to keep in mind to keep a bad hire from happening.
The recruitment and hiring process is something that needs to be carefully considered all the way from designing the role and job description, to recruiting and vetting and interviewing, the onboarding process, performance check-ins post-hire, and also identifying the problem that is being solved with this hire.
- What does the company need?
- What is the problem that’s being solved by this hire?
- What does the company need in 6, 12, 18 months?
- What are the roles that need to be filled?
- Who are the best people for those roles? What type of person does that role need? What experience, what type of executor, what personality, what skills, what people skills, etc.?
- How does the company set new hires up for success once they’ve come into the organization?
- What is the onboarding process?
- What support is available to the people you bring on for personal/professional development?
These are some of the questions to get clarity around. A lot of these questions often get blazed over by what can feel like an urgent need to hire. Yet, considering all the points above can make for a well-thought-out recruitment, hiring, and onboarding process.
Slow down.
Recruiting the right candidate is not an overnight success story — it’s a process. Moving too quickly by anxiety-driven haste misses key elements for making a good hire and more often than not can create challenges or a mess to be cleaned up later. The cost of mis-hires can be substantial, not just financially but also on team morale.
No matter what the size of the company, there’s often haste and anxiousness to figure things out quickly. Often, this amounts to not taking the time to vet people, feeling certain about the hire, or even designing the role. Regularly, clients will reflect on a bad hire and say “I just needed to fill the seat.” Making a hasty decision on who to bring on board is sometimes fueled by the pain of a bad hire and the need to replace them, and sometimes it’s a need to fill a position before a board meeting. What happens is a compromise on the full breadth of the recruitment process because of the need for the role.
Hire for a future version of the company.
It pays to slow down and consider: What’s the problem that needs to be solved? What does success look like for the solution? If you fast forward six months from now, and you’ve hired this person, how do you know that they were the right fit (and that they were doing the role well)? One mistake companies make is hiring for today instead of hiring for what the organization will look like six months, or twelve months, from now.
New role to hire for? Research!
The research phase is the first step in the recruitment process. It can help you get clear on what the role can be and what a great hire could look like. How can you be equipped with the tools, knowledge, and resources so that you have perspective when you’re going through the hiring process? One example of this would be tapping your investors and setting up ten coffees with different CTOs across companies to get a sense of what to look for in the interview process. You walk away with more perspective and awareness of how to navigate the hiring for that certain role, as well as getting more clear about what the unique needs are for the role to be filled at your company.
Get clear on how you need this person to show up.
It’s often easier to be clear about what this hire needs to own, their responsibilities, and what their output needs to be. But, ask yourself: what behaviors do you believe will lead to their success? Distinguishing between behavior and the responsibilities or accountabilities on the job description gets you thinking about how someone is getting the job done as well as what’s the what — the goals and objectives — that they’ll be accountable for.
What are the types of leaders you want in the company?
If you’re hiring for any type of management leadership position, lean into this question: what are the types of leaders that you’re wanting to bring in? How do you expect these people to grow and develop and build their teams? How are you making that a pivotal part of the interview process and selection process? Filtering for a person’s ability to grow and scale a team and lead people are crucial when hiring for management, VP, and C-suite roles.
Silver bullets and flashy resumes can fall flat.
One of the biggest pitfalls we see founders and executives fall into when hiring for crucial roles within an organization is becoming enamored of someone’s resume — such as where they’ve worked, who they worked with, or where they went to school. The common thought is “We need someone who’s done that to come in and do the same thing here.” With all that cred, they must be good, right? Yet, the one thing those shiny resume objects blind us to are thinking about cultural fit. The question to ask is: What kind of leader is going to thrive and be a fit in this organization? Without considering that question, that big gun with a great resume could cycle through your organization and leave a trail of damage in a short amount of time.
Build cultures of diversity.
Another variation on this theme is hiring someone who looks like you on paper. Academic types will be impressed by other academic types and Ivy League degrees. The assumption is that there is a certain brain trust coming out of a certain institution, or a certain shop of a certain status (like for instance, Google). An academic CEO may tend to hire academics, but in addition to asking “is this meeting what the company needs?” the other question to ask here is: “Does this add to a culture of diversity?”
About to fall into this trap? Ask yourself: What’s the story I’m telling myself about what it means to have this person and their CV come into the organization? If any of that’s at play, you may discover the desire to hire this person is to meet some inadequacy that you may fundamentally be feeling about yourself.
Shape the search.
Evaluate the full breadth of people you’ve looked at for this function. Are you missing places where you could actually seek out great talent? What exactly does this person need to do for your organization? Shaping the search for candidates is the upfront work it takes to get intimate with what exactly your specifications are for this role, for this person. Develop an internal committee around how you’re going to engage the person’s qualifications. Design the interview arc in a way that best serves your needs. By carving out a job spec that is real for you, related to your culture, and that you developed from scratch with a committee that you’re going to score against as you look at the network of candidates is worth the legwork when it comes to finding the right candidate for the job at your company.
The onboarding period is a safeguard.
Sometimes your gut can tell you something different about a candidate that speaks louder than the urgent need to fill a role with what appears to be a suitable candidate. Once you find a person you want to move fast to bring on board, and your gut is having question marks, use your onboarding process to suss out fit. The onboarding period gives you the first 90 days to get to know talent, and if it’s not working out, they’re out.
How can you set this up? What are the safety levers you have? If within two weeks someone is not a great fit, give yourself permission to say this wasn’t the right move and move on. An onboarding period gives you the flexibility to learn and observe this person in the environment and make a decision. Another way to think about this, depending on the level of role, is how can you test them? Consider working with them on a contract or project basis to see them interacting with you and your product. This can also help you assess if you need this role as a permanent fixture in the organization, especially if things are moving quickly. It can prevent you from succumbing to the ‘tyranny of the urgent.’
Check references.
Once you’re ready to bring someone on board, or hopeful they will accept the offer, it’s a good time to ask: have we checked their references? This can be tricky and require discretion of course if the person is currently employed someplace else, but you can do a backchannel through a connector that knows them. Ask the candidate for names that are safe. You learn so much from people that they’ve worked with or that know them, both good and bad. It can really tip the scales if there’s a tie between candidates or even help prevent a wrong hire. On another hand, checking references can help you learn how to best set this new hire up for success. Talking to people that have worked with this person can help you understand them better, and how to set them up for success, and how to provide them with the kind of support they need.
Reflect on how roles shift with the new hire.
Often, a leader can have a bit of an ‘identity crisis’ once a person gets hired, especially if the new hire was taking over some of the responsibilities the leader had. The deep existential questions lurking below the surface around the hiring of this key role for many leaders are: “What’s my value going to be? How am I going to contribute to my own company? What’s my role here?” In hiring a new position, leaders can feel that their value is diminished in some way, even if that is not the case in reality. If you can recognize this line of thinking, or fear ask yourself “What might I lose that I value if I hire these roles?” After spending time with that question, then ask yourself: “Who do I want to be if I have this person? What will my role be and what value do I bring?”
How do you know when it’s time to hire?
Deciding when to hire depends on circumstances. In a rapidly scaling organization hiring may be happening all the time. In other situations, a team might be hiring for a key executive role. Much of hiring depends on funding available and looking at what the company needs as it grows. If there’s a pain point in the organization that would be eased with the right hire, that’s a worthwhile hire to make.
Two things that also contribute to hiring: 1.) what are the projects that you need to move the needle on, and 2.) Who, if you hired them, would have the most domino effect on all these puzzle pieces that you’re trying to drive forward? Some other questions to consider in light of these two pieces are: Looking six months to a year out from a product and business standpoint, where do you want to be? What are the key milestones and projects that you want to have completed? What do we want the internal experience of our company to be like? What will the needs be in order to drive this work of the people and the internal company experience? What are the people that you’re going to need to hire today in order to accomplish that work given your funding? If you were to prioritize those roles based on the output that you want to create, who should you be hiring?
Where’s Your Head of People?
Most often, the Head of People positions are an afterthought, but there is much that falls under this role that makes it a worthwhile hire sooner than you think. What most teams cobble together with payroll groups, PEOs, and coaches, can eek along only so far before it begins to break. But if one of the core jobs of founders is to be thinking about recruiting more often than not, that should be reflected in their calendars. How many coffees, how many meetings are taking place in the name of recruiting? Founders are busy folks. Having a Head of People person on the team can take that job off of their plate. In fact, your Head of People can take over many (if not all) of the tasks we’ve talked about here.
Implement a strong onboarding process.
The onboarding process is just as important as the recruiting process. Once you’ve made a crucial hire or any hire, your onboarding process is how to set those people up for success within the organization. It’s important to find out a few key things before everyone is moving at Mach three with their hair on fire. What do you really expect from this person? How do you want them to feel as they transition through these couple months? What do you really need to learn about them? What motivates them? What are their strengths? What do they value? How do they like to receive feedback? What are the conditions of working that allow them to really thrive? How do they want to grow at your company?
A good onboarding experience is not only a great employee experience, but it’s great for the leader as well to know how to talk and shape the conversation with this person as they unfold in their work — as they continue to give and receive feedback, work on projects, meet new challenges — in the first three months and moving forward. Once you have these grounding conversations, what are the habits and practices that you want to use to make sure that this is going to integrate and be a part of ‘the week-over-week how you’re leading this person’?
Designing the first day.
After all the courting that can happen in the recruitment phases, all too often a new hire’s first day on the job falls flat. How would you want to design someone’s first day so that they know who their key stakeholders are, who their team members are, where the bathrooms are, and how are they going to get the knowledge of the company and the systems that they need? While some larger companies may have week-long training programs, regardless of size, there are fundamental things that someone needs to share with a new hire so they can get situated, feel confident, and be able to move fast. If not you, then who else can also support you as you’re setting this person up for success? As part of your culture, you get to design and implement your own way of giving people the key things they need to know so that they can get working and be productive. What’s the best way you like to communicate the nuances of really helping them join up?
Actively Recruiting.
Some leaders think talent will just come to them. They put up a job description and wait. But for the best talent, you have to seek them out. You have to go hunting. If you’re a manager, an executive, or founder, a huge portion of your job should be recruiting. To normalize what this means from a time perspective, anywhere from 30% to maybe even 60% of your week should be spent on recruiting. It’s an active part of your job, not an annoying thing to do on the side. Your company’s success hinges on successful hires. What might it look like for you to actually be strategic in your sourcing or hunting to get the right talent you want? How are you sourcing? How are you reaching out to the type of talent you need? How many coffees are you having a week? What’s your game plan?
Engaging a search firm.
If you’re thinking of engaging a search firm to support your recruiting process, see if you can find the person within the search firm who’s placed people similar to what you’re looking for. But don’t stop there. Stay an active part of the process. When the firm starts the search, don’t leave it to them and hope that they are the silver bullet answer to the solution. Good practice is to talk to them about what’s working and what’s not. If you interview someone that you think is off, walk through how they found them and why you think the match is not right. Remember that you’re co-creating the search together, and that may include many course corrections along the way. Be in communication with them more often than you think you’d need to be so that they don’t waste your time presenting a lot of mismatches. Be ready to call off the search if it goes on too long.
Hopefully, these points and questions will help you consider your recruiting and hiring in a way that meets your needs and the needs of the organization. With care and consideration, you can avoid the pitfalls we commonly see when leaders and their organizations go through in the recruitment and hiring process.
