How do you crack the mentoring puzzle at scale?

Over the last 5 years of working with startups, I discovered the hard way that outsourcing mentoring to external volunteers doesn’t work well. Over fifteen cohorts of startups - at Microsoft, and Upekkha, we’ve repeatedly found that founders were unable to take advantage of stellar, world-class mentors, who were themselves fellow entrepreneurs, investors, and who were committed to helping the startups succeed.

The tough lesson we learned was that unless a mentor deeply understands the founder and startup well enough, most advice is too shallow. But only a few mentors were able to go deep enough. Even if they were fully committed to helping the startup on their journey, they didn’t have the time to spare to spend going deep with founders.

As we struggled to understand this, we decided to go deeper into what was good mentoring and how we could repeatably, scalably, deliver high-quality insights to all our startups, from our world-class mentor pool.

The unknown unknowns

There are known knowns; there are things we know we know. We also know there are known unknowns; that is to say, we know there are some things we do not know. But there are also unknown unknowns — the ones we don’t know we don’t know. — Donald Rumsfeld

First, we realized that mentoring is about helping a founder know their ‘unknown unknowns.’ Once founders know their blind spots and biases, they need help to prioritize digging into the now ‘known unknowns.’ So, really, a mentor’s role is to help with unknown biases, blind spots, and gaping voids that are invisible to the founders. The catch here is that to do this, a mentor needs to spend 8–12 hours with a particular founder! This is an unreasonable ask, even for the most committed mentors in our pool.

So we decided to change the model.

We became the ‘family doctors’ who spent 10–15, even 20+ hours one-on-one with each founder, using four strategic frameworks to peel the startup onion, while creating deep meaningful connections with each founder. Once we did this, we were able to identify individual biases, blind spots, and ‘unknown unknowns.’ These conversations also help the founders become more self-aware and realize where they need to pay more attention.

And the known unknowns

After we identify the ‘unknown unknowns’, we help the founders prioritize their ‘known unknowns’, create specific problem statements, and identify the right subject-matter experts who can quickly assist. The conversation with the subject-matter expert becomes far more straightforward: there is very high value transmission in a very short time, leaving both the mentor and mentee satisfied.

For example, one startup had founders who were all from an enterprise sales background, doing a mid-market SaaS product. Busy as they have been signing up customers with field sales, they’ve been blind to what it takes to grow a serious inbound/inside sales team and processes.

Once we had this conversation, it quickly became apparent that this was a major weakness, causing them issues with their VC & fund-raise. They then crystallized the problem statement to ‘create the core inbound process for lead-gen in the next six weeks,’ and we connected them to an alumnus who is among the best in India at inbound marketing. They were able to accelerate their learning in just 3–4 half-hour sessions with this subject-matter expert mentor, and got a playbook, a hiring guide, processes, and deep feedback, which helped them build a solid core for their inbound process.

Another example: a founder had been unsuccessful in raising a VC round for more than a year. Through our conversations, we concluded that there were multiple problems here: two different product offerings to two different market segments, a lack of a clear market sizing, added to this the lack of fitment between the market segment and the marketing channel.

On top of all this, one of the founders was himself a bottleneck in most of the activities, and this was causing a slowdown in their growth. The reason he was a bottleneck was his inexperience at hiring more senior functional professionals.

Once these issues were identified, the founders were assigned different mentors for each problem, an entrepreneur in their market who could help with product definition, a VC who could help with market sizing, and a marketing expert to identify the right channel. A senior entrepreneur who had successfully built strong second-level teams was also tagged as a mentor. He gave a hiring guide and also helped structure job descriptions and interview questions.

This form of mentoring has shown a dramatic increase in satisfaction scores: I would attribute it primarily to our family doctor plus super-speciality doctor model.

If you’re a startup mentor

1. Understand the startup context and constraints, and try to enumerate all their problems
2. Help them identify their ‘unknown unknowns’ and their blind spots.
3. Help prioritize their problems; what is their most critical bottleneck for this week/month/quarter?
4. Get them help with that bottleneck — or help them yourself.

If you’re a founder with good mentors

1. Identify the areas your mentor can directly help with, where they can be a sounding board, and where they have a network. Build this map.
2. For each meeting, go with a specific challenge with sufficient homework, and data collection
3. In the meeting, start from where you are today, and where you’re going. Then show how this is a critical problem on that path.
4. Try to become more self-aware, work with your mentor to identify your blind spots, weaknesses, biases.
5. Get actionable outcomes from every meeting and document them on email.
6. Circle back to the mentor with the outcomes, positive or negative, from the actions.
7. Success ??