Nick Francis: Calibration, War Council, High Agency Investment | Work 20XX Ep 62

Nick Francis: Calibration, War Council, High Agency Investment | Work 20XX with Jeff Frick Ep62
English Transcript
© Copyright 2026 Menlo Creek Media, llc.
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Cold Open
In three, two, one.

**Jeff Frick (Host):**
Hey, welcome back everybody. Jeff Frick here coming to you from Running Remote. Another collaboration between Work 20XX and the team at Running Remote. Liam and Egor and Ana, and we're really excited to be back for our second year, as it starts getting loud here in the Quonset hut in Austin. We're excited for our next guest. He's Nick Francis, the Chairman of Help Scout. Nick, great to see you.

**Nick Francis (Guest):**
Yeah, I'm still getting used to that title, Jeff.

**Jeff Frick (Host):**
Well talk us Let's start there. So you started this thing I think you said 15 years ago.

**Nick Francis (Guest):**
Yeah. 2011.

**Jeff Frick (Host):**
And recently decided to move out of the the CEO job to take a chairman job. And I think I heard in a podcast this is the first time in a very long time you might wake up on a Monday morning and not have something immediately to do. How did that decision come about? How's it going so far?

**Nick Francis (Guest):**
You know, I spent 15 years building the company. I'm so, so proud of what we created. My co-founders still work there and I'm still involved on a regular basis. I just felt like it was time for someone new to take on the reins. It's been 15 years and it's time for me to do something new so we'll see how it goes.

**Jeff Frick (Host):**
So, I know one of your things you're doing to to get you going on the next chapter is spending time with other founders other CEOs, and bringing those folks together. Because I know being a CEO can be a lonely can be a lonely job a lot of time you know you got just tough decisions that maybe you can share, maybe you can't, so one, if you could share a little bit about the the journey of a startup CEO.

**Nick Francis (Guest):**
Sure.

**Jeff Frick (Host):**
And then how you're, you know taking that lessons and helping some of these other folks that are just getting started.

**Nick Francis (Guest):**
Yeah. There's no support built in to the org structure for the CEO, right. When you're at the top of the org chart that's when it gets, to use your words, lonely, right. And so there were two things that were transformational on my journey that helped me grow and mature as a CEO. One was having a coach. So somebody who has helped me able to help me see around corners, who was able to give me hard criticism when I needed it without any threat of organizational dynamics or power dynamics. And so having a coach And so having a coach be able to speak into the day to day, and some of the challenges that I was facing as a leader to run a 360 to get a sense of to run a 360 to get a sense of what all of our stakeholders thought of my performance and then also what was transformational for me was having a CEO peer group that was really close a group of friends and people who trusted each other who were going through the same stuff and to be able to kind of work with them to figure out like how to lead to be inspired by how they lead. And so today I actually facilitate that CEO group, And so today I actually facilitate that CEO group, and I get to work with founders just to try to give back a lot of what I received for 15 years as a CEO and try to offer that sort of support so they can be successful.

**Jeff Frick (Host):**
I'm curious what kind of the mechanics are in terms of How big is the group? How frequently do you meet? How long are you together when you meet? What's kind of the pacing to make it really worthwhile for you?

**Nick Francis (Guest):**
Yeah. So the OG CEO group that I was a part of for years we meet together once a month and then we actually spend time in person for a few days every six months and so otherwise there's just like a chat in Signal where we're kind of talking through hard things that are going on in the companies and trying to figure things out together, but being able to to have a group of seasoned professionals that share a lot of the same values as you. So that's typically what's most important in a CEO peer group is a shared sense of values. a shared sense of values. And so these people are all people that we founded our companies together like 15 to 17 years ago.

**Jeff Frick (Host):**
That's great.

**Nick Francis (Guest):**
And we've been trying to build things for the long term. And so that's very different from a founder that might just be looking for the next exit, so that shared sense of values gives us quite a bond. And we're able to to add a lot of value, help each other out.

**Jeff Frick (Host):**
So from the outside looking in it feels like today is the most chaotic moment that we've ever lived in. For lots of different reasons. But I'm sure everybody feels that way in all the moments that they exist. With the benefit of hindsight in this group over 15 years and the companies they’ve developing. Is this the craziest time we live in? Or is it just the one that we currently are inhabiting? Or, you know, are any things fundamentally different in how you're instructing CEOs to in how you're instructing CEOs to to run their businesses and take care of themselves and take care of their people.

**Nick Francis (Guest):**
I think this is a pretty fundamental shift. So, you know, I was a very I was much younger when the internet came around. [laughter] That's the only thing I can

**Jeff Frick (Host):**
Really, yeah.

**Nick Francis (Guest):**
a little more grey hair

**Jeff Frick (Host):**
A little less salt, a little more pepper, right.

**Nick Francis (Guest):**
Yeah, but that's the only thing I could really compare it to because I was learning to code right when the internet came of age. And boy, was that an incredibly exciting time. And boy, was that an incredibly exciting time. And it feels a lot like that here. I'd say that the pandemic was another big shift. So in the last six years, we've seen two fundamental kind of tectonic shifts that I didn't see the previous ten years before that. And so I do think that we're navigating something very significant. But as opposed to the pandemic which was pretty scary lives were at stake lives were at stake this one's largely very exciting. And there's a lot of really great tools that are enabling things that we just would have thought would have been magic you know, as many as 3 or 4 years ago. And so for an entrepreneur, this is heaven.

**Jeff Frick (Host):**
Yeah. One of the concepts that came up in the last keynote. Speaker was talking about having he called it his ‘War Council’

**Nick Francis (Guest):**
Yeah.

**Jeff Frick (Host):**
And he had like a grumpy CFO and an overly enthusiastic customer representative. So he had assembled a group of virtual personas to help him think through challenges. That's got to be a huge benefit because I've always said the hardest thing for a CEO to get is bad news. 'Cause nobody wants to share it until unfortunately, maybe it's too late to do anything about it. So you got to be thinking, wow, So you got to be thinking, wow, maybe I can actually have a trusted confidant with the context of the company that I don't necessarily have to put anything at risk to get some of this constructive negative things that I want to be aware of what's going on?

**Nick Francis (Guest):**
Yeah. Wade [Foster, CEO Zapier] is operating at the bleeding edge. It's funny you brought up the War Council because I use that same skill. Believe it or not, he shared it with me. And it's an incredible way to think through big decisions that you have, or even small decisions that you have to make as a CEO. And so a lot of times, you know, you're not going to get advice from your colleagues in the job or like the hard news.

**Jeff Frick (Host):**
Right.

**Nick Francis (Guest):**
Or like maybe, the here's why you shouldn't do this. And the War Council is quite effective at giving you like different perspectives. And so the way it generates like three other perspectives, and each one is making a bet as to whether you think this they think it's the right decision and it's really great to have that that sort of perspective. So these tools are just so, so fun to use. And yeah, they do operate as great copilots. I feel like my work is just higher quality as a result of leveraging them.

**Jeff Frick (Host):**
Right. So in your talk, you talked about calibration across the organization calibration across the organization in the context of a question as to What is performance, right. What are we trying to get to and what are we judging people on? And your point was very interesting that it's not a steady state, and that we constantly need to be making sure that everybody is on the same page going towards the same direction having the same values. It's not static, right?

**Nick Francis (Guest):**
In a remote company at least in my experience hard conversations don't tend to happen as often unless they are part of your operating system and your operating model as a company. And so you need certain healthy accountability practices that normalize and make space for hard conversations to happen in a safe space. And calibration the thing that you were just referencing is just a way of managers and leaders getting together and saying like here's where I'm evaluating an individual. Does that seem right? And literally aligning on what great looks like. You might have a rubric of all these jobs and descriptions, but are you actually stress testing them on a regular basis alongside other managers to determine what success looks like? And by doing calibration you minimize bias in the organization and you really are able to improve your rubric. It's not just a document that sits in a static place it's actually dynamic, it's being updated. And so calibrations are just a way for managers to get together and agree on that.

**Jeff Frick (Host):**
And was it a formal process on a formal timeline? So that was you’re not doing anything wrong, we do this right, we’re doing it all the time.

**Nick Francis (Guest):**

Yeah so it's part of the performance review process Yeah, so its part of the performance review process for us at Help Scout it was every six months. Managers in a given function all get together and they say, okay where did we land on performance reviews for all these individuals? Does anybody agree or disagree? Right. And so by doing those calibrations, it's tough. You got to be vulnerable. But it's really for the best for the company and for the employees to get another look at how your performance is being evaluated.

**Jeff Frick (Host):**
Because I think you talked about too, you know kind of breaking apart the tasks and the roles of the individual and trying to keep an eye on the ball which is organizational success. You know let's not let's not get over wrapped up on the measures what we need to keep focused on what really the true objective is.

**Nick Francis (Guest):**
Yeah I think that's really at the core of this AI transformation in this moment that we're in right now is you know a framework that I've heard that that really resonated with me is that the job is still the job, but the tasks are going to change radically. So as it pertains to being a software engineer or a designer those are still jobs and very valuable ones in software companies. But boy, the tasks associated with getting that job done and doing it well are changing in a radical way.

**Jeff Frick (Host):**
I love that framing. I love that because because of the tools and everything is changing, the data you have underneath is changing but the job of whatever that top level objective is still is the same.

**Nick Francis (Guest):**
Yeah, it’s lot of fun.

**Jeff Frick (Host):**
Yeah, good framing. All right. So another thing. Gallup recently released a workplace report. I think like 1 in 4 people or 1 in 5 people reported being ‘not engaged’ at work. It's a huge problem when people are not really checked in or checked out. You talked about on stage focusing on the right people, on engagement so that your high performers are the people that are engaged and giving you that marginal effort. How did you kind of make sure that they're engaged? How did you focus on engagement? Because I think that's such a it's such an unlock. If you can get people pulling on the oars just 10% harder, 15% harder 20% harder and if they're doing it it's not for you it's for the other person in the boat, right?

**Nick Francis (Guest):**
Yeah.

**Jeff Frick (Host):**
We know that for sure.

**Nick Francis (Guest):**
You know, there's two sides to engagement from a management and leadership perspective. You want to invest in every single person in your organization and ensure that they can do their best work at your place of work, right. But the reality is that not everybody is going to be able to do their best work in your company. And so I try to look at it as look, we're going to invest in this person the greatest possible extent. But when we look at engagement data we're typically there's a lot of feedback given to the organization that's anonymized. And so you're just getting this anonymous feedback about what you need to do better. Effectively what we do at Help Scout is we remove all the low performers from the engagement data and we only focus on feedback from the high performers. And that doesn't mean we're not invested in getting low performers to be high performers.

**Jeff Frick (Host):**
Right.

**Nick Francis (Guest):**
But, when In the aggregate when you're just looking at a bunch of data I think it's really important to focus on your high performers and spend most of your time making sure you're creating a culture and an environment that's exciting to them.

**Jeff Frick (Host):**
Yeah, that one. That one caused a little controversy in the in the crowd and the questions.

**Nick Francis (Guest):**
Yeah, I'm okay with that.

**Jeff Frick (Host):**
I think people thought you were leaving the low performers behind and you're just like no, you got you got resources. Focus where you're going to get the highest ROI.

**Nick Francis (Guest):**
Yeah, engagement surveys. A lot of people don't see the other side of the engagement survey where you just have a bunch of anonymized data and you're trying to see the signal and you're trying to be able to find the forest through the trees. So I think in those cases, it's really important to just bifucate it and say, look, I'm only going to focus on comments from the high performers.

**Jeff Frick (Host):**
Right. Other thing that you talked about, which which resonated with me is you talked about the fun part of being on the steep part of the learning curve which is good if you're in tech because it feels like we're always on the steep part of the learning curve.

**Nick Francis (Guest):**
Right.

**Jeff Frick (Host):**
And just when you think you got it. There's something new that comes down the pike. How do you inspire that within your people? How do you inspire that within your people? How do you keep that curiosity and that drive for curiosity hot in the in the culture of the company? Because if you're not thinking that way, you're not going to last very long I don’t think.

**Nick Francis (Guest):**
Yeah, that's certainly something that's innate to me as an entrepreneur. And it's hard for me to realize sometimes that that's not how everyone operates. that that's not how everyone operates. There's this word that's come up as part of this sort of AI transformation moment that we're in and it's ‘Agency’ right. People who have high agency or high level of curiosity with regard to learning how these tools work and learning how these tools can help them do better work and be more performant in their jobs. You know, it takes a lot of agency in order to kind of make your way to the other side and see some of the benefits of this tooling. And it's true, like all we can do is kind of show like do as much show and tell as we can and say, look at this incredible thing that we've built. Look at what AI is making possible in our organization. And the more you can try to socialize those things and create a safe space for people to use their agency, I think it's there in everyone in some folks, it might just be dormant. You got to wake it up. But all of us have the capacity But all of us have the capacity to be high agency individuals that can add massive value to a business, but you've got to unlock it for yourself. It's individual, and there's only so much the company can do to bring it out.

**Jeff Frick (Host):**
Right, right.

But you said, you know giving them the tools like one of your quotes earlier was, give, you know Use all your tokens.

**Nick Francis (Guest):**
Yeah, yeah.

**Jeff Frick (Host):**
Right. Don't leave any of it on the field to mix analogies.

**Nick Francis (Guest):**
Yeah, well I think there any leaders that are just thinking about leveraging AI to cut costs and improve productivity, or are to cut costs and improve productivity, or are that's a pretty short sighted view. I think we're in a moment where we need to be doing a lot of experimentation and we need to be learning it as fast a pace as we can to How what the what the next phase of this world looks like and

**Jeff Frick (Host):**
Right.

**Nick Francis (Guest):**
Man, to just be using it to cut costs. It seems like such a sad way of approaching this whole thing.

**Jeff Frick (Host):**
But it happens every time, right?

**Nick Francis (Guest):**
Yeah.

**Jeff Frick (Host):**
I mean, that was the initial cloud, you know deployment and all these things. They always start with the cost cutting and the efficiency. And it's the smart person in the corner that says No, we can build a new business or we can transform our business, or we can do something now that we can never do. And, you know, get on that top line growth number and stop worrying necessarily about saving money because you can't save to grow.

**Nick Francis (Guest):**

Yeah, bring everybody along. And I think that's the key to to growing the business and having a lot of fun along the way.

**Jeff Frick (Host):**

Well, Nick, thanks for stopping by. Congrats on your next chapter. I have a feeling you won't be just counseling other people for very long before you jump back in and get your hands dirty.

**Nick Francis (Guest):**

Thank you, Jeff. I think you're probably right.

**Jeff Frick (Host):**

All right. He's Nick, I'm Jeff, you're watching Work 20XX at Running Remote. Thanks for watching. Thanks for listening on the podcast. Catch you next time. Take care. Bye bye.

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**[Cold Close]**
[applause]
- Awesome.
- How’d we do, Joy?
- You did fabulously.
- OK.
-  Well done.

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Nick Francis: Calibration, War Council, High Agency Investment | Work 20XX with Jeff Frick Ep62
English Transcript
© Copyright 2026 Menlo Creek Media, llc.