Learnings: Long-Term, High-Value Clients

In the continued quest for offer-market fit, I've got some new service offerings at https://opportunitylabs.io. The core promise of the new offers: We'll make your business a household name to 6,000 prospects in 6 months. If that would be interesting to you, we should talk.

A few weeks ago before yet another leg of my Tour de Montana [1], I hosted a roundtable on the topic of long-term, high-value clients. I quite like the roundtable/pop-up online event format, and when the topic and audience are a good fit, the format is a real banger. Here are some notes on the event format:

  • I did zero selling on the roundtable. Two prospects for my coaching services approached me afterwards anyway.

  • 120 minutes is not too long of a duration, but a 90-minute duration might have put a subtle pressure on us all to be a bit more concise in our communication.

  • At the same time, it's possible to too-quickly or superficially discuss things. This is one of the more wily challenges this format presents. For the host/moderator it can feel like improv or performance art in that you have a group of people show up, many of who you don't know, and you're hoping to create an experience most of them get educational value from. Under those circumstances, how do you keep the pace brisk and the discussion meaningfully deep?

  • Anything you can do to help attendees feel safe or encouraged to transition from attendee to participant is potentially valuable. The event I ran was 120 minutes, and at about the 50-minute mark and about the 100-minute mark I stopped the discussion and made space for introverts or those who maybe had been sitting on something they wanted to say but hadn't felt an opening to say it. The feedback was: love this. I also let folks know that it's fine to "lurk" for the whole call if that's what they wanted.

  • I tried something totally new for me: Instead of asking every attendee to introduce themself at the top of the call, I provided a Google form where anybody who wanted to be known to other event registrants could just drop their contact info and a little context on who they are/what they do into the form and then I shared the resulting spreadsheet with all call registrants [2]. This saved a ton of time, but did make it a little harder to contextualize some comments from those who participated. Tradeoffs! I think I will definitely use this approach again in the future, but perhaps with stronger urging for people to contextualize their comments a bit more robustly the first time they comment on something.

  • I could have done a better job of preparing attendees for the roundtable's agenda. On the one hand, I wanted to remain fluid and adaptable as the discussion happened, so I didn't want to have a too detailed or rigid agenda. But in prioritizing this, I might have deprived the group of the opportunity for more of us to show up having already put deep thought into the key questions we addressed during the event.

  • Choosing to not record the event seemed to be an OK approach. I'm not confident this enabled next-level deep sharing, but I do think it sent the signal that the event was a place that requested and benefitted from everybody's best effort at presence and focus.

Here are some thoughts on the content of the roundtable (long-term, high-value clients):

  • No one had a repeatable formula for creating these kinds of client relationships. Of course, the lack of any extant formula of this kind is why I convened this roundtable in the first place! And yeah, some part of me was hoping someone would show up and drop exactly this kind of formula in front of the group. It's fine that that didn't happen.

  • There's an interesting tension between two approaches to offer design: Approach 1: you purposefully start clients on a small/limited scope/low risk service that is probably diagnostic in nature, or delivers some initial planning or design work. You then work to upgrade those clients to a more long-term engagement. Approach 2: you just offer your meant-to-be-long-term-service right from the jump. I hope I'm not mis-remembering this part of the discussion [3], but I sensed a definite preference from the roundtable attendees for Approach 1.

    • I am generally very suspicious of zero-sum thinking, but there certainly are specific situations where we can't have things both ways; we have to pick a direction and go with it and trade the benefits of the other direction to get the benefits of the direction we've chosen. I get the sense that you can design your business to appeal to long-term, high-value clients but that direction probably requires you to forgo some of the benefits of Approach 1.

  • Related to the above, I got the strong impression from the roundtable discussion that if you end up working mostly with long-term, high-value clients, you also tend to start those relationships by doing quite a lot "for free". This "free stuff" might look like any of the following:

    • Spending a lot more time in semi-structured exploration with a prospect before there's discussion of specifics or before you submit a proposal.

    • Delivering the exact kind of value you would deliver while "on the clock" for a client but doing so right from the jump with a prospect. [4]

    • During a project, being willing to do out-of-scope stuff knowing that it's good for your client and trusting that it's good for your long-term prospects.

  • This "free stuff" thing is a chicken-and-egg question. What comes first? Do profitable long-term relationships allow you to be generous with prospects, or does choosing to be generous with prospects make profitable long-term relationships more likely?

Roundtables like this one are nice ways to explore important topics where there's no obvious single best practice. I hope to host more of them in the future for y'all. Thanks to all the most excellent folks who participated!



  1. Driven further west by the need for better medical care options for my wife, we're in Missoula now. So far, we like it here. It lacks some of the dramatic mountain views more readily available in Bozeman and Paradise Valley, but more than makes up for that in having coffee roasters who understand the superiority of a light roast, better sandwich shops, more trees, fewer $80,000 Jeeps driven by spoiled college students, and 370 parts-per-million more patchouli in the air. Who knows, maybe we'll stay! Missoula also has the best cannabis dispensary name I've ever seen: Prescribed Burn. Any Missoula locals on this list? If so, I'd love to hear from you.

  2. I don't think Zoom makes it easy to know who actually attended the meeting vs. who registered but did not attend, so for my sanity when I was doing followup after the roundtable, I just used the list of registrants that Zoom makes it easy-ish to download.

  3. Hosting a roundtable can feel like juggling while riding a unicycle, so I may not be a 100% reliable witness about everything that happened during the event. 😃

  4. My recollection of Lencioni's book "Getting Naked" is that he illustrates this kind of approach quite well in that book.