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How is Coaching different than Mentoring?

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RCA Dog Nashville TN

Like many people, I confused and conflated “Coaching” and “Mentoring” for many years. In business (more broadly), and in the tech/startup/entrepreneur community (more specifically), mentoring is everywhere. We’re all encouraged to seek out and serve as mentors. I’ve benefited from incredible mentors, and I’ve mentored hundreds (thousands?) of individuals over my 25+ year career as an employee/manager, founder, investor, and advisor.

In 2022, one of my mentors asked if I would coach some of the high-performing/potential employees at his company, and I jumped at the chance. But first, I told him, I wanted to learn more about what it takes to be a high-impact coach, and to unlearn some of the bad habits that may have crept in over the years.

I researched coaching training programs, invested hundreds of hours in study and practice coaching, and, before the end of 2022, got certified by the International Coaching Federation. It was a LOT of work! I also signed my first paying clients and am now growing my clientele by the day/week/month. I’m proud of what I’ve accomplished, and I look forward to expanding my impact.

ICF Associate Certified Coach Badge

But to the subject of the post, what is the difference between Coaching and Mentoring? In its simplest form, this is what I’ve learned:

  1. Mentors (and consultants) spend much more time telling people how to do things than listening, asking questions, and being curious. This is often deemed more time efficient if the mentor/consultant is truly an expert in an area, but it can lead to advice whiplash for individuals when they get non-stop conflicting advice from a host of mentors.
  2. By comparison, coaches are trained to ask their clients questions, to help them discover their own answers, opportunities, and new paths. This coaching habit took me longer to buy into than most because I was so used to sharing my genius (sarcasm intended) and solving problems for people. Many (including me) ask, “why would someone pay a coach and then not seek their advice?” The truth is that the coach often doesn’t have (or need) all of the background/domain knowledge, and instead is there to help the high-achieving client sort through ideas already percolating in their head.

Of course, books (and thousands of blog posts) dig into this distinction in excruciating detail. But that’s the gist of it. It isn’t to say that some coaching sessions/engagements don’t combine a bit of both coaching and mentoring, but it’s important for a coach to be aware when they are switching into different roles. In fact, it’s recommended that coaches call out these transitions and to even get the client’s permission before doing so.

Did this answer the primary question/distinction? What did I miss?

What mentors expect of mentees

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mentor-mentee-changing-future

After last week’s post on “How to Be a Good Mentor“, I received a mail from the wonderful and talented Andrea Li (she’s part of the AWS Startup BD team) asking how to be a good mentee.  She asked:

  • Do you have any tips on what good mentors look for in mentees?
  • How does a mentee make it easier for a time-strapped mentor?
  • Mechanisms? Ways of communicating? Topics? Agenda?

You can tell Andrea’s a star, in that she even thought to ask this question.  To show respect for the mentor’s time investment, she immediately thought about more than just her own goals.  That consideration, and her ensuing preparation, will go a long way toward creating a mutually rewarding mentor/mentee relationship.  And the recommendations below apply very similarly to boss/employee interactions as well, so consider them as a way to improve your one-on-ones/relationship with your boss.

How to Be a Good Mentee

  • Communicate an Agenda/Topic – it helps if you have a specific topic you’d like to discuss.  For instance, maybe you’d like help developing a Career Development Plan.  Or, maybe you have questions about how to improve your interviewing skills.  If you can explain the meeting goals in advance, and send any documents you’d like the mentor to review (time permitting), that will show a respect for their time.  And if they don’t feel qualified on the topic, the mentor can politely decline and save you both some time.  I much prefer specific topic-driven meetings vs. open-ended coffees.
  • Drive the Scheduling & Stick to the Time Request – if you ask for 30 minutes, make sure you show up early and be ready to go.  And end on time.  You don’t want to be the reason their day got derailed.  And, of course, make the meeting location convenient for them (near their home, office, etc).
  • Don’t Request Too Much – Build the relationship slowly.  Make it easy for them to opt for either a fixed (i.e. monthly) schedule, or one that is more intermittent, driven by when you have specific topics you’d like to discuss.  Don’t make bigger asks until you’ve developed trust.
  • Don’t Assume the Mentors are Right – my friend @Micah suggested this one, and it’s really important to remember.  While the mentor may have a little more/different experience, it’s entirely possible that their advice is wrong.  So, take all of the advice with a grain of salt, and figure out what works for you.  This is a little easier when you have many people giving you varied opinions.
  • Follow Up on the Meeting – If you asked for their assistance with your career development plan, let them know how it went over with your boss.  Call out some specific suggestions that really made a difference.  The mentor will be happy that their time investment is paying off for you in positive ways.  Of course, remember to thank them for their time.
  • Find a Way to Help Them – you may feel like there’s little you could do to help your mentor, but if you think creatively, there’s probably a way.  Maybe they have questions about some new websites that the youngsters are flocking to.  Or, possibly they’d like some unbiased feedback about a new product their proposing.  Of course, you can always thank them publicly with a LinkedIn Recommendation, calling them out as a helpful mentor (that reflects well on them from a career perspective).
  • Pay It Forward – this mentoring thing only works if you continue the tradition.  I often tell startup founders that the best way they can help me is to help the next batch of founders.  Not only does it take those coffee meetings off my plate 🙂 but it makes the overall network stronger.  And, soon enough, they’ll recognize the questions coming their way as identical to their current challenges. Then, they can pass on that hard-earned wisdom!

As ever, what did I miss?

How to be a Good Mentor (6+ Mentoring Tips)

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The Techstars Barclays Accelerator (in London) is kicking off and that means that mentoring season is upon us. And although I’m doing my best to ‘just say no’ to anything resembling work in the near-term, I’m still meeting regularly with a few founders and early-stage-career folks every month. In fact, I have a mentor session (facilitated by awesome London VC, LocalGlobe) in an hour, helping a young woman develop her near-term career plan.

So, that had me thinking about what I’ve learned about mentoring over the last 10+ years, and why I’ve continued to invest the time.  Assuming you’re interested in the topic, I also recommend that you read the Techstars Mentor Manifesto — I haven’t read it prior to writing this post, so that it wouldn’t sway my own thoughts, but I try to read it at least once per year, as it gets my head screwed on straight before all-day mentor sessions.

These are my recommendations for being a good value-add mentor (in a startup-specific capacity):

  1. Listen (aka Shut Your Trap) – you’re not there to tell them what to do.  You’re just as likely to be wrong.  And they’ve thought about their idea for a long time.  Admit that you would have told the AirBnB team that they were nuts.  And you’d have told Uber to pivot to something else.   So, squint your eyes and ears, to see if they’re creating the future.
  2. Ask Questions – these will often help the startup team think about their product, or their situation.  This can often be a way to make suggestions without criticizing.  And by answering your questions, you’ll help the founders prepare for the same from investors, potential employees, the press, and more.  And those questions will possibly impact their product roadmap.
  3. Be Supportive – founders have enough fears and insecurities; they don’t need yours.  I’m not recommending lying to them.  But be tactful with your feedback.
  4. Give Honest Feedback – This is the complement to ‘Be Supportive’, and why I try to be brutally honest.  I try to ask questions, explain my perspective, and then get back to listening.
  5. Qualify Your Feedback – always remember to qualify your feedback with “this is just my opinion — see if others share the same…”.  Because they’re likely getting conflicting opinions from legions of people with opinions.
  6. Be Willing to Be Helpful – if you have an intro or lead that you think can materially benefit the founder, offer it (but don’t make it without getting approval from both sides).  Do not be an over-introducer!

That’s my short list.  I’m sure I missed a bunch, but if you follow the above list, you’d have a positive day for both you and the founders.

What did I miss?

What job should you take, or company should you pursue?

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Pick a job by finding a great manager to follow

This question comes up in various ways, multiple times per month, and it came up in a chat I was having with Seattle angel investor Ken Glass today as he mentioned giving similar career advice to some students recently.

Either it’s someone asking me whether they should go work for a startup, or for a big company. Or it’s someone who asks me my advice about which job opportunity to take (or pursue), when they have several options.

My answer is almost always some variation of, “go for the option where you’re working with the best boss, and the best team, and for a company/product that you’re excited about.” Don’t optimize for salary, or even title; and potentially pick your 2nd or 3rd choice company, if it means working for a star, and with a great team. If you do pick well, you’ll follow that person’s rise through the organization, and you’ll have more opportunities than you know what to deal with. That same great manager will make sure you get exposure and recognition for your efforts. And they’ll tell you when you screw up, and help you avoid repeating mistakes. They won’t sugarcoat this important developmental feedback, and you’ll love them for it.

It’s hard to exaggerate how much leverage this simple choice can make, as it can fundamentally alter your career trajectory in good or terrible ways. I’ve seen people make the wrong decisions, and you can literally see the ripple effects through their resumes for years and decades. And at the same time, I regularly see it in positive ways with young stars — making these smart choices early on will benefit you for a lifetime.

Want Entrepreneur Advice over coffee? That’ll be $1,000

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I’ve been wrestling with this one for a while, and I think many entrepreneurs have as well. See, as soon as you start a company, raise some money, and launch your business, suddenly people want to ‘buy you coffee/lunch’ to ‘pick your brain’ and ‘get networking introductions’.

I can appreciate that. I did it too. But, when you’re accommodating (as I, Andy Sack, Marcelo Calbucci, Joe Heitzeberg, and many others try to be), you tend to get overwhelmed with the requests. And, then, my days disappear on me, I end up working nights to catch up, and sit here on the weekend with 5-10 favors in my inbox which take 1-2+ hours to complete (I met with a woman last week, who I really liked… I told her I’d be happy to make some intros… she wrote back with 9 companies in the list… acck!)

So, here’s my offer:

  1. I’ll meet with you for free, at Hops and Chops (I helped organize it for exactly this purpose… sort of a lightweight office hours… I think Andy Sack created Seattle Open Coffee for the same reason) or another Seattle startup event that I happen to attend. I’ll be happy to talk with you, give you advice, and make any in-person intros, assuming the other folks are there in person. But, that’s it. Don’t ask for more, because it comes at the expense of my family, loved ones, and personal sanity.
  2. You pay me $1,000 for up to 3 hours of my time talking with you about entrepreneurship. That will likely be spread over two 1-hour meetings, and another hour of my time making introductions, if I think they’re warranted. If I don’t, I’ll be honest with you, and we’ll spend that last hour working on your plans, or whatever. Then, when you’ve started your company and booked your first $1,000 in revenues, I’ll give you $700 back. That’s it. I want you to get off your ass and build whatever it is your dreaming up. But, if you don’t, I keep your money, because you took up 3 hours that I could have been spending on other tasks. Sound fair? Do I think my advice is worth $100-333/hour? No! But, you seem to think I’ll help you somehow, and I likely will — and, if you don’t want to pay, there are tons of other folks around who will surely help you.

I look forward to any feedback about this setup. I’m sure it will upset some, but I’m not sure why — I’m still out there, and incredibly available. But, there’s now a market rate on my “premium services”, and it comes with a 70% refund, assuming you deliver the goods!