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How To Actually Be Helpful to Early-Stage Founders

What Mentorship Looks Like When A Company Is Barely A Company

This post is an excerpt from longtime startup mentor and Pear Operating Partner Touraj Parang’s onboarding session for Pear Accelerator S20 mentors — handpicked industry experts who we personally match with each founder in the cohort. Interested in being a mentor? Reach out!

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Build the Foundation: Get to Know the Team On a Very Personal Level
Establish a Heartbeat
LISTEN LISTEN LISTEN
Be a Good Coach and Look to the Future

By now, “let me know how I can be helpful” is such a cliched offer to founders in Silicon Valley that it’s become a Twitter meme. Being helpful to founders is often framed as a means to “network” in the Valley, or to become a successful angel investor, but the best mentors, like Touraj Parang, do it out of true love for the founder journey.

Touraj began “mentoring” as an entrepreneur in the mid-2000s via getting together with other entrepreneurs and sharing best practices. After selling his startup, he began angel investing, and being helpful was a natural thing to do for the founders he invested in. Over time, he shifted to simply advising without investing for the love of it.

“I personally like to know: what are the latest technologies or what are people thinking about? How are they trying to solve these tough problems? I take satisfaction in being able to help other entrepreneurs achieve their dreams, paying it forward. Lots of people mentored me and helped me, and so I feel like that’s the way Silicon Valley works.”

Especially at ground zero, companies can barely look like companies. It’s a different ballgame from mentoring more advanced companies. Touraj draws on his hard-earned years of wisdom to share best practices for mentoring founders at the earliest stages of a startup.

Step 1 — Build the Foundation: Get to Know the Team On a Very Personal Level

Most early-stage founders are struggling to answer very similar questions or challenges:

How do we grow the team? Who do I need to hire? What do I look for in a new hire? Is it how much culture matters? How much of a stickler should I be about culture if I need someone now?

How do we find that product market fit? What is really even my core value proposition? Who is my customer? Do I sell to bigger customers and a more expensive product or to smaller customers with a cheaper product?

“A lot of these questions are very much existential. It’s just picking a direction and not knowing which way to head,” says Touraj.

Fundamentally then, mentoring an early-stage entrepreneur is almost like being a therapist. Your role is to help founders figure out what their values are and who they want to be in the context of their company.

There’s no right answer to these questions, and that’s why it’s so critical to know the team on a very personal level.

So, before you even get into the idea, the market, the competitive landscape and all the other fun things about the business you’re working with — really get to know your founders.

“You really want to try to see the world as much as you can from their point of view. Because then you can actually help put things in a language that they understand or motivate them in a way that they would really click with it.”

What is their background? What have been some past challenges or extraordinary achievements that they have had? What are their personal aspirations and ambitions? Try to probe into their areas of strength and what they consider to be their weaknesses, individually and as a team.

Understand what success looks like to your mentees. Capture their initial goals, even if they are vague, and start from there. Though many similar challenges come up with early stage founders, the founders themselves are likely all very different.

“I try to level set initially and understand, ‘Where are they coming from?’, and then be responsive to where they are, and meet them where they are, rather than just having uniform advice for everybody. I try to be very mindful and personalize the guidance I give.”

Step 2 — Establish a Heartbeat

Part of building a solid personal foundation with your mentees is to establish a rhythm of the relationship. Whether it’s a weekly or biweekly meeting, put it in the calendar right off the bat. Hold that slot in your calendar and make sure your mentees put it in their calendar and stick to it.

Once everyone gets busy, it can be very easy for the weeks to go by and lose that thread. While it’s understandable that the meeting may need to be moved occasionally, do all you can to hold your mentees accountable to showing up for the meeting, and make sure that you do your share and stay available as well.

Step 3 — LISTEN LISTEN LISTEN

Once you’ve established the basics, the key skill to being a successful mentor is to be patient and practice being an active listener.

Active listening to me is not only hearing what the person is saying, but then asking questions to get to the deeper layers of what they’re struggling with,” says Touraj. “It’s engaging in a dialogue and withholding advice until you understand the root cause and what the objective is that you’re trying to achieve in that conversation.”

When a founder first comes to you with a complaint about a situation, the root cause of that complaint is often not clear. Sometimes founders struggle because they’re not clear on what goal they need to achieve. Sometimes they know their goal, but they don’t know how to achieve it. Some founders are very detail oriented but have a hard time of going higher up and looking at the big picture. Some founders are so academic and big picture that they don’t really see the operational steps necessary to get where they want to go.

You want to create a space for open dialogue so that you can get a clearer picture on the situation.

Get into that mode of investigative work. Part of that is nudging them by asking probing questions.”

Some example questions Touraj suggests:

  • What do we learn from this outcome?
  • What hypotheses are we trying to validate?
  • Are there other solutions to the same problem?
  • What you’re putting your efforts into — is that the highest priority?
  • Do you have resources to be successful? If not, what do you need and in what order?

Note that through all of this, your role is NOT to tell your mentees what to do. Remind yourself to address the assumptions, rather than making assertions. Try to stay away from ‘You need to go do this.’

“It’s good for founders to know your role is not to provide answers, but to be a thought partner, to be a sounding board. Let them draw the conclusions. Once you clarify the assumptions and the goals, they can come up with how to get there and sometimes they come up with it much better than you could.”

If the founders are hitting roadblocks or feel stuck, a helpful approach is to suggest options. You might say, ‘In other companies I have seen, these are some of the things that others have tried. Which one sounds good to you?’

Touraj notes that newer entrepreneurs can be hesitant to open up about their problems.

“They feel like because Pear is an investor or potential investor in the next round, they always have to give the happy talk and seem confident,” says Touraj.

“You have to make them comfortable and say ‘Look, it’s okay. It’s okay if you have challenges. We have all had challenges, and it’s actually a good sign that you have challenges and you’re seeking help, rather than trying to white-knuckle it and then fail.’ They need to feel that they’re not being judged in any way, and that really, as a mentor, you’re here to help, you’re not a secret agent of the VC firm.”

Step 4 — Be a Good Coach and Look to the Future

When you’re working with early-stage founders, remember that you are also working with future leaders. As such, for maximum impact, go beyond the therapist role and take on a coaching mentality.

“It’s about seeing what skills we can give them, so that they become great entrepreneurs and leaders as their startup grows. I try to encourage a lot of reflection and self improvement,” says Touraj.

One way to do this is to train your mentees on best practices that you have found useful in your own life or in the organizations you have worked in. Although Touraj was an entrepreneur, many of the processes and frameworks he shares come from his experience at larger organizations like GoDaddy.

Touraj also works to hold his mentees accountable to their own goals.

“When we are meeting, I always make a point of writing down every goal, or every statement they make saying that they will go and do certain things. In my next meeting, I refer back to those and make sure to see whether they were done and if not, why not, so that they get this habit of accountability — if they say something, if they commit to something, they’ll follow through with it.”

In setting their own goals, however, founders may not be stretching themselves or taking enough risk. A good coach will figure out exactly how far they might need to push a founder. The best coaches help their protégés achieve things they didn’t know they were capable of.

“I think one of our jobs is to encourage founders to be bold, to experiment. And that it’s okay to fail and to learn as long as you learn from it.”