Mentorship At Early Stage Startups (And Beyond)
Updated: May 7
We can learn from people who have gone through what we’re going through. The mentorship provided can be a simple comment on an airplane, a lunch, a series of calls spanning a few months, or a life-long relationship where we learn from one another.
Mentorship is a symbiotic relationship. Each party is getting something out of the relationship. Because a lot of things we do is about motivators, let’s look at what each party gets from such a relationship: The person seeking mentorship receives knowledge handed down from a mentor about a small slice of what we do for a living or about an entire industry. Knowledge they don't have to learn the hard way. This helps with the journey ahead. The mentor gets to think more deeply on an aspect of their own journey, maybe come to terms with the parts they didn’t do well and maybe share the parts they did do well in a form of euphoric recall. Many also just really enjoy mentorship and sharing experiences, given that it can be quite rewarding.
Learning from one another is an important aspect of mentorship. But another aspect is networking. Both parties can provide valuable contacts to the other. Each party might be in a place to help the other by passing their contact on in the future as well. But helping one another is at least in part altruistic as well. Both parties need to be willing to accept insights from the other and act on them. While we aren’t responsible for triggering others we can be gentle about how we go about handing out feedback.
Being a Mentor
Founding a company means wearing a lot of hats. One hat that we’re likely to wear for the life of the company (or at least our involvement and maybe beyond) is mentoring. Mentorship is not career or life coaching. But it’s not-not either of those either. We often pay coaching but mentoring comes with a different set of expectations and results.
Mentorship comes in many forms. As founders, we can put the types of mentorship provided in three primary categories:
Skills mentorship. This is how to be better at the specific tasks a position requires. This might be insights into how to more successfully implement a given framework in code, rejection handling tips on sales calls, or asking whether we can help with anything else on a support call. These are skills and while the technical skills are easier to train, the soft skills require more finesse and a deeper understanding of what people are going through.
Role mentorship. Beyond skills, we want to mentor people on how to better handle their roles in the organization. Here, we can ask questions that lead to a deeper understanding of how a role contributes to the organization, how to improve the role, and how to improve interactions between a given role and others.
Career mentorship. We also want to prepare for growth. This means not only growing the organization but also preparing the next generation of leaders (whether technical or managerial) in the organization. Here we seek to understand the motivators and gaps between where someone is and where they want to be.
We can also help with work-life balance. But notice that we’re not helping people with their personal relationships or finances. For personal relationships, there’s therapy and for finances there’s apps, financial planners, and accountants. Instead, we’re helping them navigate how to get all of the things they need to get done and to improve professionally. We can do more as friends but there are boundaries and we all have permission to define them when crossed.
One boundary that’s easy is where we actually can’t help our coworkers. As founders, supervisors, managers, directors, or friends, we don’t have to provide mentorship. Maybe we just hired someone in a role we know nothing about and simply can’t offer effective and impactful guidance to grow one or all three of the above mentorship categories. Here, we can use our network to find others who can help. Maybe there’s someone on the board of directors or they can offer a contact. Asking a mentor how to find mentorship opportunities is a great way to spend time receiving mentorship - and for the record if we’re not being mentored it’s going to be difficult to see good and bad mentorship techniques ourselves.
Now that we’ve explored areas of mentorship, let’s look at some things we can do during our time with those we are mentoring. The time we spend mentoring is about others. Servant leadership often is. Here are a few things to make sure to do each time we meet with those we mentor:
Ask questions. This is the most important thing we can do. Open the floor for those we are mentoring to get what they need out of the relationship. Open ended questions are best in the beginning, unless we need to get a point across and then a closed ended question followed by a “why” is a simple tactic to allow others the agency to find their own answers (with a little guidance). We don’t have to have a set path the questions will take us on, but we can.
Listen thoughtfully. As others tell us of their challenges and goals and ask for feedback, it’s easy to provide flippant responses. This isn’t about us talking, it’s about us providing quality feedback.
Share feedback. Our feedback is why people are coming to us as mentors. The questions and active listening are really to get to a deeper understanding of what others need. That feedback can come in the form of ideas for further exploration and growth opportunities, but we have to keep in mind that our experiences may be different so we can share them but also need to leave room for what others are going through. Be direct with feedback, but not offensive.
Provide examples. Telling stories is a great way to reflect on what we’ve been through and allow others the benefit of understanding where our experiences are concentric. This can be a trap as many mentors go straight into storytelling without first really listening and providing feedback.
Offer to make introductions. We might not be able to provide assistance with something but an introduction either to someone who has been through a similar situation or a vendor who can assist with a need is a great way to help without overextending our advice into an unknown area. For example, let’s say someone needs to build a community and we met a passionate community organizer - we can make an introduction rather than dwell on an area we aren’t really experienced at.
Set and reflect on goals. A final aspect of mentorship is keeping honest about our goals, motivators for the goals, and progress towards them. This isn’t always necessary and could overlap with guidance our teams are receiving from front-line managers but it’s always good to understand these and to try and keep the rest of the conversation aligned to the goals when possible.
Don’t get frustrated at any slow progress, but also hold people accountable. We’re here to offer encouragement. So keep in mind that we all grow at different paces. We have to be patient with others on a different path, as they may have areas of personal growth or family challenges they’re dealing with outside of work. We want to help people progress and set goals but life can be complicated so need to give room for that. And hopefully at some point our mentorship will be less effective because people have outgrown what we have to offer. At that point, it’s time to find them a new mentor who can help with their next set of challenges.
If we manage to scale the organization, over time we will have less time to mentor those outside our senior management team. When we feel like there needs to be more mentorship in an organization, it’s time to get a bit more formal and create a program for our brave adventuring party to get help where they need it.
Creating Mentorship Programs
Mentorship programs are really easy and really hard to start. It’s fairly easy to tell a company or community that there’s a mentorship program and define rules, like a person responsible for matching people asking for mentorship with available mentors, or recruiting mentors.
Most mentorship programs fizzle out over time. The sponsor of the program moves to a new position or the organization doesn’t get a quantifiable value from the program and the program dies out. But we hope there’s a lasting impact, while not quantifiable, in how the guidance provided grew various people in the organization.
Don’t have time to think about or do anything with mentorship programs? That’s probably not a good sign but it’s worth mentioning that there are alternatives to building these out ourselves. Check out torch.ai or chronus.com - or work with a local academic institution (like an MBA program) to get more community engagement.
Finding a Mentor
The last aspect is really about finding mentors. This might be a founder recruiting a board member who’s also a mentor, finding mentors for our teams, or information we can provide our teams for them to find their own mentors. Mentors are people who have had success in a given career path OR navigating the dynamics to get what’s right done inside a company.
Mentors can be found in a number of places. Consider the following:
Technical or management leaders in our organization. Here we can work with people in positions to provide feedback about the organization and what it takes to succeed not only in a role but in our careers at the organization. This might be a founder in an early stage startup and then as we scale to 100 people or a given revenue metric for an industry that might shift downstream.
Similar roles in other organizations. We want to avoid talking too much with competitors about what we’re going through. It’s a shame but true. Instead, we can look for other titles in similar organizations. If we’re a new Sales Engineer we might find a sales engineering manager at another organization to talk through what the role entails routinely. There are lots of roles that are similar between organizations like software developer, accounts receivable, etc. Domain experts might be best matched with people who have successfully navigated either remaining domain experts at a high growth organization or pivoting into a different career path, such as product management which often becomes more diluted when those with product experience rather than domain expertise join the organization.
Similar types of organizations. This doesn’t mean competitors but instead other organizations on similar trajectories. For example, when joining a recently funded, hyper-growth startup, it helps to have mentors from other rapidly growing startups at a stage beyond where we are in order to understand how to navigate that journey in a way that befits the organization while serving our own individual needs (without of course putting our needs over those of the company). One tactic here is to find other companies that just got funded and researching people in similar roles at those organizations. Most companies in each series of funding are similar, despite the domain expertise and mission. Company building can be its own assembly line that way. There are nuances with B2C or true enterprise or companies who are downmarket from an enterprise player (or upmarket from a true consumer play) - but the similarities and shared experiences are more than many think.
Academia. Business schools and other research organizations have a wealth of advice to hand down. Many in technology startups might be suspicious of academics (which goes back to the 1970s personal computer revolution when a guy like Jef Raskin pretended he didn’t have a PhD when interviewing at Apple, then coming up with the idea for the original Macintosh so proving his value). However, there are plenty of professors or post-docs just looking for hot new startups to drop some wisdom on!
Career coaches. Finally, we can hire a career coach. Coaches come with all sorts of backgrounds and some veer more into life coaching, but it’s important to find someone we can talk through our issues with and coaches are a great resource for the right scenarios.
While finding a mentor, we need to be candid with them and ourselves about what we want out of the relationship. We might not really know yet - and that is fine. But we in order to maximize the impact of the relationship for both parties we should be as forthcoming as possible. Maybe we have a single meeting or maybe we meet for years - they’re all valid and hopefully remain mutually rewarding for all parties.
As a company moves to each stage of growth with each series of investment or revenue milestone we have to take off a hat or three - so the best mentor can probably be the one who can help us decide which of those hats we’ll keep wearing and navigate the next stage. Over time, founders and those we add to the adventuring party that is our company will hopefully learn to be deliberate about which hats we keep and which we remove.