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Posts Tagged ‘hiring

Hiring Your First Product Manager

picard-and-rikerAs a technical or product-focused CEO/founder of a growing company, a challenge one eventually faces is making that first product manager hire. Like most founders, there’s a good chance that you’re seeing ongoing challenges balancing the ever-increasing workload as CEO and starting to feel that sense of distance from the product as the needs of sales, marketing, hiring, and more pull you away. You might be wondering how you can spend more time on what you love, the product, while recognizing as CEO you must grow the strength of the organization while also focus on the contributions that you can make uniquely from the CEO role.

This is where making the first product manager hire is necessary and also a unique challenge. Most of the time, this hire is postponed as long as possible. You can cover-up for this missing resource with additional late night mails, some extra last minute meetings, and so on. The time this really hits home is when feature work or decisions turn into re-work or re-thinking. That’s the sign it is time to hire some help. Engineering resources are precious and timelines are always tight—being the founder-pm-bottleneck is no way to iterate your way to product-market fit.

The short answer to this next step is two-fold. First, at an emotional level this is extremely difficult for most every founder (btw, in a big company if you are starting a new product team it turns out this same dynamic applies). It is likely you will talk to quite a few candidates and no one will ever seem quite right. Second, you are going to have to trust your team a great deal on the fit and in doing so adjust your own approach to product management as part of the on-boarding process.

Every situation will be unique and there is no single rule for what type of skillset, experience, or seniority will be right for you and your company. The most important thing to think through before you start the process is to agree between your co-founder(s) and team on the profile of the role you wish the new PM to play in the organization.

Traditionally this would be framed along the lines of a job description:

Seniority. Are you looking for a VP, Director, Lead? Most typically you start here but these descriptions might fall short of really defining the role and so you end up seeing a lot of candidates.
Domain. Perhaps you are looking to fill in a specific technology background as part of this hire? As the product evolves you might be expanding into product areas that could use additional strength from product management. The question is really how much this will change the bottleneck you might be seeing.
Skillset. Are you looking for a candidate with more of a design, project management, or engineering background?

Each of these are examples of necessary but not sufficient criteria in kicking off the search for your first product manager. Because the first product manager hire is so unique for a product-focused founder, it is worth offering a framework or characterization of the role that you might start with.

Once you arrive at characterizing the role, then you are in a better position to narrow the search by more traditional experience and skills descriptors. Each of these below can work with the key being clear on hire and in management what the expectations are for the new product manager.

Extra hands. Most every founder I speak with starts the description of needing an extra set of hands, eyes, ears—someone to offload some work to, follow-up, track down, etc. This is often a positive stop-gap and can certainly work short term. Medium to long-term it can also starve you of the opportunity to grow the organization or might mean you set yourself up for yet another product management challenge down the road. If you go with this approach then the important thing to watch is that you did not solve you bottleneck problem by just moving it to another person or adding a level of bottleneck-indirection.

Process chief. Are you looking to offload the unpleasant or less intellectual aspects of product management such as the details of tracking, documenting, and other “process” issues? It is quite natural to be very narrowly focused in hiring the first product manager to want this set of skills added to the team. It isn’t uncommon for engineering to also seek this addition. The good news is this is almost always helpful. The challenge is it also adds another person to the team for the short term but might not really reduce the load or bottleneck but could unintentionally add friction to the process. A careful balance is required.

Apprentice. Many times the goal of bringing on the first product manager is to reduce the risk of hiring a senior or experienced person and going with a relatively junior hire and working to grow him/her into the role that you actually need. This can often be the most comfortable approach for the team because there’s a clear view of who the boss is and relatively clear expectations with the new PM. Generally the challenge can be down the road when you bring in more product managers and have to decide if the apprentice is “senior enough”. To avoid this challenge the best thing to do is really put in place a true training and growing situation. You need to provide the right level of responsibility and feedback/mentoring. Sometimes the difficulty is in hiring at this level but expecting too much, too soon.

Mini-me. Another model I have seen is searching for that first PM that is a reflection of your own skillsets and experience—a mini-me. For many this younger-sibling approach can be comfortable and easy to model and understand. It is a matter of finding the candidate that shares your product point of view and vision, and then a way of getting it done. The interesting challenge with this approach is not the way it works, but the way it might not work. Will the new PM amplify not just your strengths but your weaknesses? Will this miss out on the chance to being more perspective, diversity of thought and approach, or new ideas into the team? Are you being imitated or copied?

Successor. The most difficult or bravest first PM hire is to hire your successor. In hiring this person you’re bringing on a person who will simply be the final voice in product management. This is a scary approach and depending on the direct responsibilities you have and where you are in the product-market fit journey this might be the best approach for you and the team. The challenge I’ve seen most often with this first hire is that the seniority level doesn’t quite match the organization yet. The new hire’s first step is to build out a team and bring on more people. This might be exactly why you’re bringing on the person (just as when you bring on less familiar functions) but generally isn’t the case for product management as most often the first hire needs to be hands on and will buy you some time or runway. On the other hand, often the right candidate comes along—one who has the right level of person contribution, domain knowledge, and scale experience—and that might make for the right fit.

Of course hiring the person that fits this description as well as all the right product skills could turn into a unicorn hire, so definitely be careful about over-constraining the challenge. Of course, hiring is just the first step. As you onboard, assign and delegate work, and manage a new product manager you will also need to be incredibly deliberate in your own evolving role in product management. All too often the most-fitting hires can run into challenges when there is a mismatch between intention and execution of product management responsibility.

One word of caution. If you are concerned or even “afraid” of hiring a strong product person with a point of view, perspective, or just streak of stubbornness then think for a moment. Are you labeling the person a poor fit for “culture” or are you actually more concerned that they might make your own personal transition more challenging? If you’re working to always bring on strong people, don’t compromise at this juncture.

Hiring the first or early product managers for technical/product focused founder(s) is always a big step and a difficult one. When done correctly it can be a positive and rapid accelerator for engineering and a positive for the company overall as it makes room for you as that leader to focus on the work you can do uniquely.

Steven Sinofsky (@stevesi)

Written by Steven Sinofsky

April 7, 2015 at 2:00 pm

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That First Sales or Marketing Hire

The A-Team TV showOne of the biggest changes for an early-stage and growing company is when hiring transitions from technical/product founders to the first sales or marketing hires. It is an exciting time of course but also one that can be very stressful. As much as that can be the case, there are a few patterns and practices one can follow to successfully cross that chasm or at the very least reduce the risk to the same as any technical hire.

It goes without saying that the challenge is rooted in learning how to recognize and evaluate talented people that possess talents and skills that you do not have and really can’t relate to from an experience level. Quite a few roles in companies are going to be “close” or adjacent to your own skill set, speaking from the perspective of a technical founder. If you’re an engineer then QA or product management aren’t far off from what you do on a daily basis. If you tilt towards product management, you’re interactions with designers are perfectly natural. In fact for technical founders the spectrum from design to product management to engineering and then QA all feel like your wheelhouse.

Branching out further to sales, marketing, communications, business development, customer service, operations, supply chain, manufacturing, finance, and more can get uncomfortable very quickly. I remember the first time I had to interview a marketing person and I realized I didn’t even know what questions I should ask to do the interview. Yet, I had worked with marketing closely for many years. Fortunately, I had a candidate pipeline and an interview loop of experienced interviewers to draw from. That’s not alway the case with a startup’s first hires.

The following are four challenges worth considering and a step you can take to mitigate the challenges if you find yourself in this spot.

Look only within your network. When sourcing your first potential sales or marketing hire, you might tend to tap into your network the same way you would for an engineering hire. You might have a very broad network but it might not be a first person network. For example with engineering you might know people from the same school program or projects you worked on or are deeply familiar with. But with sales and marketing you probably lack that much common context and your network might reflect people you came across with in work or projects, but not necessarily worked with in the same way you would have with technical hires. You might be worried about taking too much time to source candidates or concerned that you will burn a lot of time on introductions and people you don’t “know” well. Approach. The first step in a breakthrough hire process is to make sure you cast a wide net and tap into other networks. This process itself is an investment in the future as you will broaden your network in a new domain.

Define the job by way you know from the outside. Walk a mile in other’s shoes is an age-old expression and is very fitting for your first sales or marketing hire. Your initial job description for a job you never done might be taken from another company or might be based on your view of what the job needs to get done. The challenge is that your view of what needs to get done is informed by your own “outsider” view of what a job you haven’t done before might mean. Being a sales or marketing person is vastly different from what it looks like from the outside, looking in. If you haven’t done the job you tend to think of the job through the lens of outputs rather than the journey from input to output. Most jobs are icebergs and the real work is the 90% under water. Until you’ve watched and worked with an enterprise sale end to end or developed and executed on a consumer go to market plan, your view of what the job looks like might be a sales presentation or SEO. Getting to those deliverables is a whole different set of motions. Approach. Find a way to have a few “what do you do” conversations with senior people in the job function. Maybe take some time to ask them to define for you what they think the steps would be to get to the outcome you are looking for, rather than to discuss the outcome. These “what would it take” conversations will help you to craft a skills assessment and talent fit.

Hire too senior or too junior. Gauging the seniority of a candidate and matching that to the requirement for the role are often quite tricky early on. In the conversations I’ve had I tend to see founders head to one extreme or another. Some founders take the outcome or deliverable they might want (white paper, quota) and work backwards to find a hire to “execute” on that. Some take the other extreme and act on the basis of not knowing so bringing in a senior person to build out the whole system. The reality is that for a new company you often are best off with someone in the middle. Why is that? If you hire to too junior the person will need supervision on a whole range of details you haven’t done before. This gets back to defining the job based on what you know—your solution set will be informed only by the experience you have had. If you hire someone too senior then they will immediately want to hire in the next round of management. You will quickly find that one hire translates into three and you’re scaling faster than you’re growing. I once talked to a company that was under ten engineers and hired a very senior marketing leader with domain experience who then subsequently spent $200K on consulting to develop a “marketing plan”. Yikes. Approach. Building on the knowledge you gained by casting a wide net and by taking the time to learn the full scope of work required, aim for the right level of hire that will “do the work” while “scaling the team”.

Base feedback on too small a circle. Once you have a robust job description and candidate flow and ways to evaluate, it is not uncommon to “fall back” on a small circle of people to get feedback on and evaluate the candidate. You might not want to take up time of too many people or you might think that it is tricky for too many people to evaluate a candidate. At the other end you might want these first hires to be a consensus based choice among a group that collectively is still learning these multi-disciplinary ropes. Culture fit is always a huge part of hiring, especially early on, but you’re also concerned about bringing in a whole new culture (a “sales culture” or “business culture”) and that contributes to the desire to keep things contained. Approach. Getting feedback from at least one trusted senior person with experience and success making these specific hires is critical. You can tap into your board or investors or network, but be sure to lean on those supporting you for some validation and verification.

One interesting note is that these challenges and approaches aren’t unique to startups. It turns out these follow similar patterns in large companies as well as you rise from engineering/product to business or general management. While you might think in a big company the support network insulates you from these challenges, I’ve seen (and experienced personally) all of the above.

The first sales or marketing hires can be pretty stressful for any technologist. Branching out to hire and manage those that rely more than you on the other side of their brain is a big opportunity for growth and development not only for the company but for you personally. It is a great time to step back and seek out support, advice, and counsel.

Steven Sinofsky (@stevesi)

Written by Steven Sinofsky

February 6, 2015 at 10:00 am

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Hiring for a job you never did or can’t do

imageOne of the most difficult stages in growing your own skillset is when you have to hire someone for a job you can’t actually do yourself. Whether you’re a founder of a new company, or just growing a company or team, at some point the skills needed for a growing organization exceed your own experience.

Admitting that you don’t really have the skills the business requires is the first, and most difficult step. This is especially true as an engineer where there’s a tendency to think we can just figure things out. It is not uncommon to go through a thought process that basically boils down to: coding must be the hardest job, so all the other jobs can be done by someone with coding skills.

Fight the fear, let go of control, and make moves towards a well-rounded organization.

Nice try.

If you’ve ever tried some simple home repairs or paint touchup you know this logic doesn’t work—you only need to spend an hour watching some cable TV DiY show and you can see how the people with skills are always unraveling the messes created by those who thought they could improvise. The software equivalent can sometimes be seen as a developer attempting to design the user interaction flow in a paint program or PowerPoint. Sure it can be done by a developer (and there are talented developers who can of course do it all), but he or she can quickly reach their limits, and so will the user interaction.

Open up your engineer’s mind to embrace the truth that every other discipline or function you will ever collaborate with has a deep set of skills experiences that you lack. Relative to engineering, the “softer” skills often pose the biggest eye-opening surprise to engineers. Until you’ve seen the magic worked by those skilled in marketing, communications, sales, business development or a host of other disciplines you might not appreciate the levels of success you can achieve by turning over the task to trained professionals.

I have seen this first-hand many times. Most recently it occurred while working with the a16z portfolio company Local Motion when it came time to do some of the early announcements around the fleet-management company. The co-founders possess engineering and design backgrounds from elite institutions, and built the product themselves, hardware and software. Both are experienced mountaineers, and so they have this engrained sense of self-sufficiency, which is valuable both for building companies and scaling mountains.

When it came time to work with the industry press to tell the story of their company, in some ways they had to suppress their self-sufficient instincts. The founders were self-aware enough to know they had not done this before and agreed to enlist the help of those who have depth and breadth of experience. The pros showed up and spent time learning the team, the business, and the story (professionals do that!). They came back with a plan, roles, responsibilities, and defined what success would look like. It was amazing to watch how the founders absorbed and learned at each step all those things which they had not personally experienced before.

This sounds easy and pretty obvious. But if you put yourself in their shoes you know that this is not just bringing in a hired gun to get some press, rather this is hiring on a new member of the team and a new founding member of the family. What is vital to keep in mind, is that this kind of work is as important as every line of code and every circuit board. The lesson of letting go and letting professionals do their work is clear: delegating is never easy for most, but is spectacularly difficult if you don’t know what the other person is going to do and when the outcome matters a whole lot. Still, you need to let the specialists into your carefully engineered world.

There are moments of terror. You’re watching people talk about your product using tools and techniques you are unfamiliar with to connect with your potential customers. Even though it is a product, you are apt to feel as though this is a discussion about yourself. You question every step. You doubt the skills of the person you hired. You are certain everything will go wrong.

It is at that point—right when you start to panic and think that unless you do this yourself things will fail—that you need to let go. You need to say “yes” to hiring a person to do the work, and then let them do their best work.

Just keep reminding yourself that you’ve never done the job before, and that you’re role is to hire someone who knows more than you. Even when you’ve wrapped your head around that, there are a few ways you can get tripped up when you are The key to success here is avoiding these mistakes when you are in the hiring process:

  1. Asking candidates to teach you. A good candidate will of course know more than you. Their interview is not a time for them to teach you what they do for a living. The interview is for you to learn the specifics of a given candidate, not the job function. The best bet is to do your homework. If you’re hiring your first sales leader then use your network and talk to some subject matter experts and learn the steps of the role ahead of time.
  2. Expecting a candidate to know or create your strategy. It is fine to expect engineering candidates to know the tools and techniques you use. You wouldn’t expect an engineering candidate to know your unannounced product, of course. It is equally challenging to expect a new marketing person to have a marketing plan for your product. Even if you ask them to brainstorm for hours, keep in mind the inputs into the process—they only know the specifics you have provided them. For example, don’t expect a marketing candidate to magically come up with the right pricing strategy for your product without a chance to really dive in. On the other hand, you can expect a candidate to walk you through in extreme detail their most recent work on a similar topic. You can get to their thought process and how they worked through the details of the problem domain.
  3. Interviewing too many folks. You will always hear stories about the best hire ever after seeing 100 people. Those stories are legendary. On the other hand, you rarely hear the stories that start with “we could not find the perfect QA leader so we waited and waited until we had a quality crisis.” Yet these latter stories happen far too often. Again, you should not compromise, but if after bringing a dozen or more people through a process you are still searching, consider the patterns you’re seeing and why this is happening. A good practice if you’ve not found right hire after going through a lot of folks is to bring in a new point of view. Consider recruiting the help of a search firm, a board member, or a subject matter advisor to get you over the first hire in a new job function. Do you need the help of a search firm? Would you benefit from the help of a board member or subject matter advisor to get you over the first hire in a new job function?

These add up to the quest for the perfect hire. When it comes to engineering you give yourself a lot of leeway because you feel you can direct a less experienced person and because you can gauge more easily what they know and don’t know. When it comes to other roles you become more reluctant to let go of a dream candidate. This almost always nets out costing you time, and in a new effort time is money. That isn’t saying to settle, but it is saying to use the same techniques of approximation you naturally use when hiring people in your comfort zone.

The most difficult part of hiring for a job you don’t know first-hand is the human side. Every growing organization needs diversity because every product and service is used by a diverse group of people. The different job functions often bring with them diversity of personality types that add to the challenges of hiring. The highly analytical developer looking to hire a strong qualitative thinker for marketing, or the highly empathetic sales leader, is often going to face a challenge just making the human connection.

This human connection is a two-way street. Embrace it. Recognize the leap each of you are taking. Realize that the interpersonal skills required to call on customers every day are just different than the interpersonal skills used when hacking. The challenge of making that human connection is one for the person doing the hiring to overcome. Often that’s the biggest opportunity for personal growth when hiring people to do a job you can’t.


–Steven Sinofsky (@stevesi)


Note: A form of this post originally appeared on FastCo.

Written by Steven Sinofsky

April 3, 2014 at 9:30 am

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