Turns out, I’m good at the wisdom business

Alan Jones
6 min readJul 8, 2024

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Not gonna lie, nobody’s more surprised than me about that.

As our brains age, we get less able to take on new information. It’s still possible, but it’s less automatic. The upside is that we’re more likely to be able to draw insights from what we remember in our past. That’s what’s commonly called ‘wisdom’ and it’s why we usually turn to our elders for their wisdom, not our kids.

Next January, I’ll turn 60. Not yet old enough to be a candidate for president of the USA but no longer young enough to be a no-brainer candidate for a C-level exec or cofounder role in a startup.

So as my own brain ages, I’m grateful my advice is more likely to be received by others as wisdom than it did when I began because it’s not easy for older people to remain gainfully employed in any industry (much less the tech startupindustry) and being perceived to be wise leaves me with options to serve as a board member and mentor.

Sidebar: I’m also very grateful that I’m a CIS white male. I know age is perceived differently if you’re a woman, non-CIS, a person of colour, or someone living with a disability. I see you, I respect you.

About three years ago, I decided to ‘go public’ with my mentoring and challenge myself to be good enough to make part of my living from it.

I setup a basic website at StartupFounderCoach.com (when I say basic, it may still have some lorum ipsum clinging on in some out-of-the-way sections). I used Calendly and Stripe to setup some availability in my schedule for mentoring, and some prices for my time.

Sidebar: another thing that changes as you age is that you get easily annoyed at new habitual phrases or changed meanings of words, like using the word “like” instead of silence or pauses, or starting a sentence with “Not gonna lie…”. So I have to grit my teeth to start the next sentence that way, but it is apt…

Not gonna lie (ARGGHH!) it was scary to start accepting mentoring bookings from people I didn’t know, who’d just found me online and it was even scarier to worry about what they might think about having to pay for my advice. What if they didn’t think I was wise enough? What if my advice wasn’t helpful? What if they didn’t think it was good value-for-money? Could I even bear to ask the question, much less hear the answers?

To dig myself out of my self-doubt hole I drew upon the advice of Rachael Neumann, who I’d met while working as an entrepreneur-in-residence for the QUT Creative Enterprise Australia Collider accelerator program. Now she’s a widely-respected VC with Flying Fox Ventures, but 2014–2016 she successfully rolled out a company-wide NPS (Net Promoter Score) program at Eventbrite to provide a continuous feedback loop from customers and employees.

During a long but interesting walk across campus, in which I got us hopelessly lost, her wisdom for me was along the lines of, “The more it scares you to think about measuring something, the more important it is for you to measure it. If your NPS score is bad, you definitely want to know exactly how bad and why, as soon as possible.”

If I was turning pro in the wisdom business, I had to give my mentoring clients an opportunity to tell me — in a quick, constructive and non-confrontational way—what they thought about the mentoring session we’d just had.

Luckily, I knew how. Rachael had also recommended a SAAS platform designed for organisations to quickly and conveniently conduct ongoing NPS surveys. Like many SAAS products, Delighted offers a free version intended as a trial that upsells a larger organisation into a premium subscription. For me, the free version is all I need.

Calendly lets me send a follow-up email after every mentoring session, and all it does is ask the mentee to click on a link to answer a super-quick two question survey managed by Delighted:

Hey {{invitee_first_name}}, thanks for attending our coaching session today.

I’d love your feedback to help me improve my coaching. I’d be very grateful if you could answer this tiny two question survey that should take you less than 30 seconds.

You can also just reply to this email with any feedback or additional requests.

Thanks,

alan

My NPS survey really is just two super-quick questions: a Likert scale question, and if you wish, an option to add a comment.

Terrifying, right? Right. Who should want to know the answer to those two questions? I was exactly as scared about seeing the results as you probably are right now, imagining seeing yours.

So, how’d it go? Obviously, if my NPS was terrible, I wouldn’t still be in the wisdom business, and if they were just OK, I might still be dispensing wisdom but I wouldn’t be writing about my NPS results. Now I’m in year three, and my last 12 months have been my strongest yet. Like (ARRRGHHH!) really, really good.

Along the way, I haven’t heard from everyone, obviously. There will always be people self-selecting out of giving me feedback for a variety of reasons, not the least of which being people who suspect it’s not actually anonymous, even though Delighted won’t tell me who’s answering the survey questions. It is anonymous, but I can’t prove to them that it is.

I’ve learned so much about what mentees have valued in my coaching and mentoring, as much from what they don’t give me feedback on, as what they give me feedback on.

I’ve learned to be much more directive, to politely interrupt at times, and to not be afraid to repeat a question if mentee’s answer didn’t address it.

I’ve learned that having some time to think about some of the mentee’s questions prior to our session so I’m not starting from scratch when the session begins is valued as highly as the advice I give, so I use Calendly’s forms to let a mentee ask some free-form questions, or link to a document in the cloud, and ask them why they want my advice, not just what they want to ask me about.

I also use Calendly to make sure they give me enough time to think about what they’ve asked in their pre-session questions, by not allowing them to book in a time any sooner than 48 hours from the current day and time.

I suspect just asking for feedback positively influences their perception of me. We’re all tired of being asked to review the meal we’ve just had or the driver that just took us across town, but I don’t think people ‘in the wisdom business’ do it very often.

Sometimes maybe because they don’t think they have to, sometimes because they don’t know how without it being weird, and more often, I think, because they’re afraid to ask. Not gonna lie (AAARRRRRGH!) I was afraid too, but I’ve learned I had nothing to be afraid of. I’ve learned that I’m good at the wisdom business.

Have you used NPS or something similar in your non-Uber, non-hospitality industry, where seeking feedback is uncommon? How’s it working for you?

More about NPS: https://www.perplexity.ai/search/what-is-an-nps-o21tj9zkSSWeUq6RAK4_dg#0

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Alan Jones

I’m a coach for founders, partner at M8 Ventures, angel investor. Earlier: founder, early Yahoo product manager, tech reporter. Latest: disrupt.radio