Top 5 Tips for Hiring Start-Up Leaders
1. Know your audience
Candidates applying for jobs at a startup are doing so for a reason. There are benefits and risks to every company, but folks who have worked, or are applying to work at a startup are usually more resilient, flexible, and comfortable wearing multiple hats. These are potential employees who want to take risks, and they understand the potential for high reward or iteration. They understand the job isn’t only a 40 hour a week commitment, and are looking for opportunities to grow and challenge themselves. These candidates want a more transparent interview process, opportunities to connect with founders and senior leadership, and are open to and expect more alternative pay, benefits, and perks.
Large companies offer security, solid benefits, and clear lines of career development. The roles are often more shallow in scope, as they have more employees to cover the work that needs to be accomplished. These companies are much more risk averse and reward longevity and tenure. These are not bad values, just different from what is needed in a startup environment.
When you’re looking at resumes or perusing LinkedIn, remember the kind of employee you want to have to help build your business. Do you want a “company” person or a risk taker? It may appear on paper that a candidate with 15 years of experience at a leadership level would be perfect for your “Head of” role, but think beyond the words on the page. Would there be a mismatch of goals going after a potential candidate who has never experienced the fast paced world of a newly founded startup? Might this candidate be too far from doing the work (and just managing) and you need someone who can dig in and do the work until the company is ready to add a team? And likewise, don’t discount the high performing individual contributor or a more junior manager level for a leadership role.
2. Potential vs Experience
This leads into our next point. You are starting to build out your leadership team when you’re around 10-15 employees deep. You think what you need are seasoned leaders to shore up your team. Or do you? Looking back at our profile of risk takers, take a closer look at the agile workers who are excelling at their individual contributor roles and ready for the next level, but lacking the opportunity at their current organization. Or the managers at large companies who are stuck at that level because someone has to quit or die for a promotion to happen. These also include those without “manager” in the title, the team leads, informal mentors, and the individuals, who given the opportunity and training, could raise up incredible employees. These are your potential superstars! Be open to the mindset of these candidates and don’t discount them because they haven’t had a specific leadership title for 10 years.
One caution here is that they will need to know and live the cultural values of your company. Employees who have not managed employees before, or have only done so at one company may not understand the nuance of how to best manage people in different environments. And definitely not intuit how things work best at your organization. They will innately imitate the leaders who have led them through their career - for better or worse. As founders you need to set the example for the kind of leadership that will create engaged employees, invested managers, and a positive work culture. This doesn’t happen solely by osmosis, so make sure you are investing in your leaders and their development, whether new to the role or not.
3. Understand your needs today
The truth of the matter is that the leaders you are hiring today need to do more than just manage. We often call this the Player/Coach. These are the leaders who may be the first employee in their department before a larger team is ever necessary. In that case, who are they leading? The immediate focus is leading the development and design of the department, but also doing the day to day work. This is one of the hardest parts of hiring tenured leaders from big organizations - can they do the work that needs to be done, or have they been so far removed that they only know how to lead other workers? At 100+ employees you’ll need hierarchies, but do you today? Taking a longer look into your hiring plans to find the right leaders or potential leaders today that will grow with your organization.
One key idea on hiring is to work backwards. For example, look at your long term planning or financial model. Are you looking at an aggressive hiring model, or a slower growth plan? What is the timeframe for growth and what roles/departments need to be prioritized? This will help determine not only the headcount you need, but when you will need it. If you wait until you think it’s needed, it’s too late. Hiring can take a considerable amount of time and then the new employee will need to come up to speed. Ramp time will depend on the position, but plug it into your model. For example, if you know you need to hire 30 new employees in the first half of the year, don’t wait to hire the recruiter in that same time period. Planning farther in advance will make sure you have the talent you need when you need them.
4. Ask the right questions
What are the right questions? I hear so often that hiring is incredibly difficult, and “I don’t want to hire anyone who hasn’t met everyone on the team, had 12 rounds of conversations, delivered multiple projects, etc, etc.” Whew. I’m tired just typing that. You don’t need assurances written in stone to make a good hire. What you do need is to understand the role you are trying to fill, the expectations for the first year (or beyond) for this leader, and a clear set of values. So why not 12 rounds of interviews? It is imperative that you be aware of the candidate experience. A long drawn out process tells the candidate that you don’t value their time, your team is unable to make decisions, and possibly that you don’t know what you want. These negative candidate experiences not only tarnish your reputation with that candidate, but could hinder your ability to hire great talent. Be willing to take a risk and trust your own judgment.
The first step to hiring a role is a job description. What do you want this person to know, to do, and to have experienced? Think of a job description as an advertisement for the job. Think creatively. What are “must haves” and what are “nice to haves?” I have seen leaders create job descriptions that included that any candidate “must have a degree from an ivy league school”. Be careful of shortcuts that are not direct links to actual behavior. What they wanted was someone tenacious, bright, and organized - but that could be someone who worked through poverty, or limited opportunities to gain success. You must let go of preconceived notions around what is good. Good means people who will thrive in your company culture, and add to the diversity and success through their contributions. There are no shortcuts.
Most job descriptions are a boring list of responsibilities and requirements. Long bulleted lists followed by long bulleted lists. Not only does this not really stand out to candidates or give them a flavor or your culture, values, or what it would be like working there, but it has been studied that women will only apply to a job where they meet 100% of the requirements, where men will apply if they meet 60%. You don’t want to lose any demographic because of a wordy ambitious set of bullets.
Be specific, to the point, and capture their attention. Give it your culture’s personality. This is also a great opportunity to focus the posting on the kind of applicants you think would make for great employees. And above all - keep it short. A long drawn out posting will have the applicant scanning for a few things and not really taking in the whole vibe of the post you’re trying to give.
Intro: Give an overview of your company. What makes you tick? What are you proud of? What would be exciting to a potential candidate?
Bonus points: detail the hiring process. When candidates know what to expect they’re much more likely to stay in the process then when additional steps are constantly sprung on them. This is especially easy when you have already created a cohesive interview process that you use consistently in advance.
Instead of “Responsibilities”
What you will do here
What are the primary job duties and what does success look like?
This can be a paragraph style and is more a narrative of what they can expect of the job.
What influence or autonomy does this job give? Is there room for creativity or thinking outside the box?
What impact you will provide
If they will be managing a team, what is the dynamic of that team? What does it look like today, and what are the plans for growth?
How can they come in and make a big impact on success? No one should have to guess what “good” or “great” looks like in a job.
How does this role contribute to the success of the company? Employees are more engaged at work if they understand the impact of their role.
Instead of “Requirements”
Are you someone who has had extensive experience in X?
Do you have a passion for X?
Traits - ie. if extremely detail oriented is a key success to the job, say so!
Remember anything you list as a hard “requirement” and the candidate you hire doesn’t have this can open you up to liability. If they are not required, but preferred, say so.
Conclusion: This is the place to mention benefits, if it’s remote, travel needs, and anything you think would sell the candidate on applying to the job. Also note that many states now require you to post a salary range for each position.
This is also not the time to be super creative with job titles - remember key words are your friend. If you’re hiring for a sales executive, calling it a business development officer may not pull the applications and resumes that you’re looking for. Calling a job by an old fashioned name doesn’t help either. I don’t know any HR folks who want to be called Personnel. Or too newfangled, such as Chief Happiness Officer - what does that mean? I have no idea, and a candidate is going to assume you don’t either or that you don’t take the role seriously.
Reading a resume should give you the broad strokes on their expertise, experience, and knowledge. A recruiter should have an intake call that susses out these baseline abilities. For example, a recruiter would screen for technical skills required, work experience, motivation - why they applied and what would make them interested in making the leap to this role, and their working style. A solid recruiter review should be diving into the resume so that all candidates that land at the hiring manager’s desk are able to perform the requirements of the job.
So how do you focus your, most likely limited, time in an interview? Here are some questions that give you more insight into how they will lead, what they prioritize, and will they add to your culture. (I purposefully didn’t say “culture fit.” We’re not looking for a new drinking buddy, but someone to help build your company and make it great). Some questions to start may include:
What about joining the leadership team for a start up excites you? What scares you?
Gives you insight into what drives them, and what are areas where they will need support.
GREEN FLAG: Expressing prior positive team experiences, admitting they don’t know everything, and are ability to adapt to different leadership styles
RED/YELLOW FLAGS: Candidates that are unwilling to do the work, not just managing. Candidates expressing past frustrations working with other leaders.
How would you hire to build out your team? When is the right time to do so? How have you hired in the past, and was that method successful? Why? What would you do differently here?
Leaders need to understand that usually 20% of their job will end up focusing on recruiting. You want leaders who don’t delegate this away to just the recruiting team, but are actively involved, want to hire A players (not B or C players that will never compete with them), and want to be advocates for the company.
GREEN FLAG: Flexibility, a tentative plan for staffing based on prior discussions on the trajectory of the company, having a good attitude towards the hiring process and previously owning hiring
RED/YELLOW FLAGS: Candidates who say that recruiting is HR’s job, wanting to build out a large team too soon (could indicate inability or undesirability to do the work required)
How does the mission of your department and work support the overall company?
Understanding your business is key, but truly understanding the tie between departmental or individual success and the overall company goals creates engaged employees. Everyone wants to know how the work they do will move the company forward and create value. This also demonstrates that they have listened, researched, and understand your company goals and vision.
GREEN FLAG: From prior conversations understanding how their role and function ties to the company’s strategic objectives. Clearly articulating the value they will deliver.
RED/YELLOW FLAGS: Generic answers that show poor listening or researching skills. Or taking 100% credit for the overall company success (ie: “without sales you have no company” yes, but what are we selling??)
What are your core work values? How do they impact your work and your leadership style?
Do these match yours? If a candidate says that their highest work value is work/life balance, and your company is digging in on nights and weekends to get a product off the ground - this may be a mismatch, at least at this stage. Does this mean work/life balance is not a good value - NO! But it has to jive with where the company is today.
Pay particular attention to the values impacting leadership style. Are they hands off managers, but will have a team of just out of college employees who have never worked outside a summer job? This may not be best. Or do they see their job as helping employees see the opportunity and cultivate curiosity? That may be just the ticket.
Often new startups value curiosity, teamwork, grit, focus, ingenuity etc. A 50 year old company may not need “grit” to be a core value, it’s more focused on keeping the ship on course.
Sidenote - how do you interview for grit? One example would be “Tell me about a time where something you tried completely failed. What did you do next? What did you learn?” Grit is pushing forward even through struggle and obstacles. Learning from your mistakes and making different choices. It could be on the job, it could be life experiences, or school based. It’s key for many startups that will face a lot of adversity, and need people who won’t become discouraged, but push to look for other ideas and use that tenacity to move to success.
GREEN FLAG: A solid tie between corporate values, the direction of the company, and a desire to learn
RED/YELLOW FLAGS: Any response that clearly defies core company values. If a core value is teamwork, and the candidate says they can only work alone, and have no desire to collaborate, this would be an issue.
How can the founders help you be successful? If you were to leave in 6 months, what would be the reason?
Everyone who is working wants to further their career. Even if you’re the CEO, and there isn’t a position higher than you, you still want to be learning and growing. We forget sometimes that the best way to understand what someone needs is to ask! These questions get into how they want to be managed, or not managed and what are the risks if you are not in sync?
GREEN FLAG: Honesty. This question really gets to the core of frustration for people. For example, if a senior leader says the reason they would leave is that “you don’t listen to me” they are being honest about a core value that motivates their success. This will also give you insight into how they want to be managed.
RED/YELLOW FLAGS: Fluffy responses “I’d never leave, this is my dream job!” or not giving any thought to their own success with “I don’t know.”
What about your work lights you up?
I love this question. You often see someone’s face change when you ask this. You can literally see their eyes light as they talk about the part of the work that drives them. We all work for a paycheck, but when I get to do “this,” whatever that is, it gives me great satisfaction. And, surprisingly, it may not be what you expect.
GREEN FLAG: A passionate response, and one that aligns with the business or work
RED/YELLOW FLAGS: Listing something that is not part of the job. This could show a misunderstanding of the role. Or if they don’t have an answer. Do you want to hire someone who dislikes their job?
What questions do you have for me?
Notice the phraseology of this question. It doesn’t ask if they have questions, it assumes that they do. Be open and not defensive. If they ask a pointed question, answer honestly and transparently. Remember that they are also interviewing you! Candidates who have no questions, especially those hiring leaders should be a yellow flag. You want people who are curious, who question the status quo, and who will put in the work to make this the best place to grow their career.
GREEN FLAG: Asking focused questions. Showing curiosity, or clarity on the role or the company.
RED/YELLOW FLAGS: No questions. Super superficial questions or yes/no questions. For example “Are your employees happy?” Yes. Does that tell them anything? You want curious people, make sure they ask great questions.
SIDENOTE: Some leaders think that if a candidate asks about benefits or compensation at this point that they aren’t applying for the “right” reasons. Let’s be honest here, in the US having healthcare provided by their company is essential. Why wouldn’t candidates want to understand how a company takes care of its employees? And we all work for a paycheck. No one loves your company enough to do it for free.
A lot of companies have started giving projects, or “take home” assignments to prove the candidate can do the work. Recently there has been some pushback from candidates. Many may feel as though they are giving free intellectual property or work product to a company who may or may not employ them. Also, many candidates are still working full time jobs while interviewing, and their time may be limited. The best compromise, if you feel that projects are essential to hiring the right candidates, is to pay for their time. Spend time defining a project, make sure that it is absolutely relevant to making an informed hiring decision, limit the time and scope to 2-3 hours to complete the project, and compensate them for their work.
5. Trust but verify
Many companies have gotten wise to the reference check, and in an attempt to shield them from potential lawsuits they no longer give information other than dates and titles. This is not useful information outside verifying work history. It doesn’t tell you how they work and what they value. Remember that candidates generally are not going to give you references that will speak poorly about their performance. I suggest asking for at least 2 personal references (meaning they don’t speak on behalf of the company, but only on their own personal experience with the candidate). One should be from a prior manager, and one should be a prior subordinate (or teammate if they haven’t managed in the past). This helps the candidate focus on people they think will best represent their work, and clarifies that “personal” reference doesn’t mean your best friend or neighbor.
What questions do I ask to get a better sense of the candidate from these references? Here are some samples:
Tell me about a time when the candidate was struggling, and how did they overcome it?
What advice would you give me to best manage this candidate?
What was your best communication method to work with this candidate?
How would you describe the candidate’s leadership style?
What can you tell me that wouldn’t be on the candidate’s resume?
Is there anything I haven’t asked that would be important for me to know?
Listen to hear not to respond. Sometimes it’s what a reference doesn’t say that is more telling. Bring any concerns back to the hiring team to vet out. But don’t let the perfect be the enemy of the good. If you ask the reference, for example, what was their experience managing the candidate, and they don’t give you a straight answer, did the candidate actually give you a coworker or a former manager? Or if you ask if they’d hire the candidate and they respond, “we don’t have any opening” that’s not answering the question, and they may feel uncomfortable being honest. Also remember that people are people and may have their own agendas. So a poor reference could be about something other than the job performance. Ask follow up questions and vet the responses with the hiring team to really get a sense of how much you can trust the reference.
Backchannel references can be helpful, with an eye to caution. We are all growing people. Asking a friend of a friend how the candidate worked 10 years ago may not be the most relevant experience. Many backchannel references end up being more general, like “would you work with this person again?” or “were they a team player?” and this info could validate your interview process. But remember all references are A data point, not THE data point. They should be combined with your interviews and the experiences of the hiring team, with the reference as a lid on a great process, or a check on a red flag.
Okay, you have done the work, spent time with the candidate, and verified that all the information you could gather (interviews, projects, references etc.) that they are the right person for the job. Huzzah! The next step is to not only offer the job, but to sell them. Make the candidate feel not only that they are the best person for this job, but that you are genuinely thrilled to have them help you build this company. Employees want to give value and be valued. Here’s the first of many opportunities to give that to them. Let the adventure begin!
