Let’s face it, running companies is tough. Really tough. We all need a little help from time to time, whether this is our first startup or our tenth. Unlike when I started my first company back in the mid-90′s, there’s free flowing advice all over the Internet. But not all advice is appropriate for all companies, and that’s where industry knowledge, experience, and expertise matter, and I’d make the claim that there’s not a business leader on the planet who couldn’t use some form of mentor from time to time.
Personally, in my roles at Stage Two, 500Startups, the C100, and Founder Fuel, I’ve acted as a mentor for literally dozens of companies, both big and small. I really enjoy the process of getting to know the team behind a new venture, learn about their goals, their ambition, and their vision. It’s the latter that makes up a key starting point in any mentoring session – understanding vision. I feel most startups are clear on their business, their tech, their product, their market, but can rarely clearly articulate vision. My #1 tip to all entrepreneurs (first time or tenth time) is to watchthis TEDtalk by Simon Sinek. To mentors – think about your role, your process, your learnings over the years and figure out your own “must-do” items for the companies and teams you meet.
Whether formal or informally structured, I think another key thing entrepreneurs and mentors need to figure out is what they want to get out of the relationship. Oftentimes I get brought into some strategy or brainstorming session, but nobody in the room has any goal or desired outcome. The best way to get the most out of these structures is to know in advance what the targets are. Then you can get right to work, dive into the product, the pitch deck, the business model, the marketing strategy, etc, and also have some form of expectation management. This burden falls equally on the mentor to help guide the entrepreneurs as to what they *could* get out of the relationship.
It’s important to know one’s strengths. I’m known for creating great product experiences, marketing strategy, etc, but also more specifically in the consumer technology field. Sure, my experience and knowledge can lend itself to helping an enterprise company navigate some issue, but I’m sure I’d be better off finding that company someone with more pertinent advice. There’s tons of smart people out there, so try to find the ones who have directly tangible experience to what it is you are doing. And to the mentors, ditto – yes, you can probably help lots of companies, but you as well should try to focus your energy on the companies you are best suited for.
It’s just as important to know one’s resources. I’m a father of young children and work at a startup. I don’t have much time on my hands. So when a company asks for my help, I’m typically pretty clear about my availability with them. Everyone has constraints, so both to entrepreneurs and potential mentors – make sure these are well communicated.
Lastly, and probably most importantly: expect brutal honesty. I open every new relationship by saying “I trust you have friends and family to tell you how amazing you are and how this startup will change the world. That’s not my job.” There’s a great blog post on “stop being so nice” here, and I agree with it all the way. I’m not mentoring when I’m ignoring flaws in the business model, or go-to-market strategy. I’m not being helpful when I say the app “has potential.” It’s when I help dive into these issues, and keep asking the “why is that true?” or “and how exactly will you do that?” questions that I’m being a good mentor.
Now, be careful not to berate. Startups have their boards to be on their ass about whatever mistakes they are making. The mentor’s the coach, the “go give em hell, tiger” person – once the path is clear, that is. I make sure to toe the line well between finding (and attempting to fix) problems before they happen, then help right the course when the problems do happen. You never want to feel bad leaving a mentoring session, but as I said earlier, you aren’t the cheerleader either.
Finding and/or being a great mentor is a challenge. But it’s one well-worth taking.
note: originally posted on the c100 blog