Brian Elliott v3: Invest, J-Curve, Goals, Team | Work 20XX Ep43

Brian Elliott v3: Invest, J-Curve, Goals, Team | Work 20XX podcast with Jeff Frick Ep43 from Running Remote 2025, Austin, TX

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© Copyright 2025 Menlo Creek Media, llc.

Cold Open:
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Yep, alright
So we are speeding.
So we'll go
in 3, 2, 1.

Jeff Frick:
Hey welcome back everybody Jeff Frick here. Coming to you for a very special episode of Work 20XX We're in Austin, Texas at the Running Remote Conference hundreds of the leading  minds about remote work but it’s important  to always remember everything that’s good  for remote work is also good  for hybrid. Also good for  distributed teams. Also even good if  you're back in the office. So there's a  lot of great lessons. And we're excited to have our next guest who's really literally wrote the book  on this topic, and now he's writing a new newsletter. So let's check in with Brian Elliott.

Brian Elliott:
Hey Jeff

Jeff Frick:
Brian great to see you

Brian Elliott:
Good to see you too. Glad to be here with you.

Jeff Frick:
Your new company,  CEO of Work Forward. And you’ve got  a really cool and deeply researched newsletter that's going out on  your Substack.

Brian Elliott:
Yeah. So ‘Work Forward’ on Substack is my newsletter. [https://theworkforward.substack.com] It's got a combination of like all the data in my data geekiness that  people come to expect from me, but also a lot  of storytelling. Like, I just wrote a  story the other day that combined  some learnings from PagerDuty and Atlassian around workplaces, doing the piece on like how to manage outcomes, especially in distributed teams, but also the impact that has on generative AI. There's a lot of content out there that I learned from listening to people that are actually  doing the work, that are actually  leading the way, and I try to bring those stories to everybody else

Jeff Frick:
Yeah, I love it  because you are you are out talking to people. So, in fact I noted the Atlassian. Three things you  noted there was Radical  Transparency. Enforced Focus and Lightweight Updates. I wonder if you can expand on that  a little bit.

Brian Elliott:
Yeah, sure.

Jeff Frick:
I was at Atlassian Summit two weeks ago and I love their focus on goals.

Brian Elliott:
Yeah, goals focus has really been a big thing for me for a long time. In my startup days I learned the hard  way really that like if you don't  have focus on like what's the most  important two, three things for you  to get done, it's really hard to  get the team aligned. And by the way, being in a startup forces that kind  of discipline. Companies get bigger, they get sloppy, to be honest, and people don't have alignment anymore. So Molly Sands, who leads  the research team at at Team Anywhere with along with Annie Dean, she and I talked  about this in depth in terms of  what they do. So three simple rules that I really loved. Number one is  3 to 5 goals per team. And that's it  on a quarterly basis, 3 to 5 goals that  are clearly articulated, that are measurable, that you can talk about. And at least  once a month go, hey, how are we  doing against that? Are we moving forward or are we not? Where are  we struggling? What can we do to get back on track or is this  not working? So that's number one. Number two  is transparency and that's a  huge deal I can see inside  of Atlassian anybody else's goals, any team's goals. I can  subscribe to. So if there's something  going on in marketing that impacts my team, I can see how  they're doing. That takes all the mystery out of it and also means  we can actually, you know, go forward  and do better. The third one is  a little mechanical, but I've heard so many people complain Oh my God I have to do 25  updates a week in three  different systems. There's is  really simple Tweet size  updates once a  week on those  top goals. So if you think about it that way, it's like, I really just want  to make it clear what we're  working on. I want to know  where we are, be transparent and make it simple for people to do. You can go a long way in getting people aligned and marching in  a common direction,

Jeff Frick:
Right, I love it just the forced  prioritization. So the radical  transparency though can be hard for some companies.

Brian Elliott:
It Is

Jeff Frick:
But one thing, I just attended your session a little while ago that that everybody should  be able to do. You know, and you're  talking about middle managers being just burned out. Stuck in  the middle. But at the same time they're  not getting any training about this new world so What is going  on there? Why aren’t people  investing in these people?

Brian Elliott:
Yeah. So it's  really sad like I think it was Gallup that put out a survey just a couple of weeks ago saying that something like 44% of managers globally have no training whatsoever. That's just really sad when you think about it. It's not  surprising, right? People get promoted  into the job because they’re the most senior person on the team, but then they're expected all of a sudden to be a manager and you've got  no support in doing it. So that's bad. Kate Lister put out a research piece last year saying that something like 25% of managers have any management  background training support in leading  distributed teams, 75% of those managers are leading distributed teams. So we're kind of leaving them out to dry in a lot of different ways. There's simple things  you can do to address those  sorts of things, but man, you can't expect that  you're going to get better as a company and  as an organization if you don't invest  in leadership, right And especially given how fast the world around us is changing to ignore that  is like pretending that we can actually just keep on limping our way through all the dramatic changes facing us from you know, the economy  to generative AI to flexibility.

Jeff Frick:
Well, you went through kind of a Maslow's triangle of the different  attributes. And the one on the top  was a learning culture so I mean you  would think if maybe people don't have  a learning culture, they think we've been doing it this way forever, and maybe we can stay at the top of  the Fortune 500 for another 60 years. But that's not the case at all.

Brian Elliott:
No, no, some of the data that’s wild for me is like 1940s, 65 years was the  average tenure of the S&P 500. 2014 is like 17 years. So just like longevity of firms isn't there in the same way. I think a lot of people say learning culture, but they're not putting the resources behind it because you've got to make  a short term investment for long term  gains, right. You gotta be willing to say, hey, look, we're going  to loosen up this quarter's goals enough to give people actual room to get their  hands on these new generative  AI tools, for example, because they’re not going  to be more productive coming out of the gates. Right? Any time you have  to learn new skills and adapt to  new ways of working, it's going to take time and effort. If you're not willing to put a little bit of slack in the system, you're not going to get over the hump of that learning curve that's going to give you  the long term gains. But if you're gonna have a learning culture, you've got to put time, energy and resources behind it to make it happen.

Jeff Frick:
And you really focused  on that last talk about the J Curve,  that that by rule There's a downward  dip in the slope. Because you gotta learn the new thing.

Brian Elliott:
Yeah, you gotta think about this is like it's happened in  every single technology that’s been  massive and major. The initial  downward slope is it takes investment to get that good enough. And so think about this with generative AI. For the past  couple of years, a lot of what we've been doing is swivel chair, right. It’s like okay, I've got  my regular process and I'm coming over here into this other tool to figure it out. It's also people are  figuring out like What's it good at? What can I use it for? What can I  do with it? Right Those investments are going to take productivity down for a period of time. But if you believe and I do, that this can actually make you more efficient, more effective and better longer term. You have to pay that price sometime. And by the way, if you're not paying that price now one of your  competitors might be. And eventually what's going to happen is you're going to be  sitting there saying, why are my people not adopting this stuff and going faster? And the answer is going to be because you've given them no time to do it.

Jeff Frick:
It's crazy. So another really just crazy dichotomy  you pointed out was with  the difference on the investment  in customer side. Customer segmentation  customer journey, buying journey sophisticated  micro segmentation. And yet one's treating  the office like it's 1955 Mad Men. It's crazy.

Brian Elliott:
Yeah yeah So the employee experience does not get the  level of investment that customer experience does unfortunately. We've seen the  impact of technology on customers and  digital transformations and all the rest of it. We’ve not done the same thing  with employees. And I’ll give you like even workplace is a great example of that. Workplace teams have  undergone more pressure and need to transform in the last five years than anybody else. More than I.T., more than HR, more than even leaders in some ways. And I can see the difference between firms that are actually putting support into those teams to help them rethink the role of offices, right which are really  are essential for a lot of teams in terms of  team building and collaboration. They're redesigning  spaces. They may be shrinking it. They're giving people that are distributed access to more tools, but also those leaders are putting in place small teams to help. A lot of other managers who we've just noted aren't really trained to make them  capable of doing like a lot better team building with their organizations. The leaders are doing that are getting further ahead. There's about half that workforce crowd though that wants to  do those things, but their  leadership is like it's not worth  the investment or maybe they're all  going to come back. And so they're frozen in place and it's just like generative AI. The longer you wait to start experimenting, innovating, piloting out  new ways of working, the further behind  you're going to be.

Jeff Frick:
The further behind  you go So, it’s interesting,  I don't know, I think you're the first one  to really tie together the management  skills that that enable people to be  successful at distributed work Yeah are the same set of  skills and behaviors that will enable the managers to drive successful adoption of AI in their team. Which as you said,  right now, one of the biggest challenges  everybody has. I thought that was  so insightful. So what are the key  attributes that cross that line?

Brian Elliott:
Yes. We already talked about like a learning culture which sort of sits at the top of  that Maslow's structure of needs The second layer below that is ‘Team Oriented’ because there's not a one size fits all in organizations when it comes  to flexibility, right? The needs of, teams that  are in Europe is different from the US is different from China. The needs of my  engineering organization are probably different from sales. So figuring out  at the team level, how are we going  to adopt flexible work is also going be  the same thing as how does generative AI fit  in our flow and rhythms of work? So you have to invest  at the team level below that, maybe the biggest one at the end of the day, that ‘Outcomes Orientation’ we talked about in terms of like Molly  was explaining at Atlassian what they do. If you can focus on what  are our most important goals how are we going to grow our business? Then people can  sit there and say, okay, how can I use those tools to achieve growth, as opposed to hearing  the word efficiency and thinking layoffs, or from a flexibility perspective, instead of  having goals you're focused on are they  sitting in their butts in seats and being  monitored? And the base level really  at the end of the day is What's my  talent strategy? Am I after the best and brightest capable people? Am I going to invest in them in terms of training and skills? Because I know that the agility we needed as an organization is going to require really great people that are supported and feel engaged. Or am I back in command and control and telling people what to do and hoping that somehow the CEO is smart enough  to see every curveball that's coming  at them and get  past it? So that's the  four levels of this. The learning culture,  team orientation, outcomes, orientation and  what's your talent strategy.

Jeff Frick:
I confused  you there I made you go top to bottom instead of bottom to top. Very good, good knowledge. You’ve done that one a few times with people

Brian Elliott:
Yeah I can take it either direction. I've done this enough times in enough conversations. I know where the problems are.

Jeff Frick:
Well I wrote down  some of these things as you said  just to call it out, you know, outcomes versus attendance. Yeah. Objectives versus  efficiency. And you didn't  call it out. But Nick [Bloom]  called it out. And he did today  here again Nick Bloom on profit  versus productivity. Yeah. He’s like people are going  to continue on this route because it's  profitable That's right. It makes a lot  of sense for people. That's right. And the  piece of it that he highlighted  and you did to is the is retention.

Brian Elliott:
That's right. Because the people that  are most likely to leave unfortunately  for you are the ones that  are the most qualified because they're the ones  that have the other options. That's right. And by  the way, one of the things  that I love about this is we keep talking about flexibility in office workers. The same thing can apply  to frontline workers. I did a great case study on Neiman Marcus Group with Eric Severson who was the  Chief People Officer there. They actually allowed people who were store associates and operators to do some of their  work from home. So, for example, if I'm a store associate, I actually also  managing customer list and I'm  doing training and I'm doing  some merchandizing. Some of those can  be done from home. I also importantly want some schedule flexibility. They found that those investments in flexibility for frontline workers gave them literally industry  leading retention numbers, that kind of retention number, by the way, also shows up in the bottom line of organizations. So you can make those investments. And this is not just an  office centric thing. You can do it on  the frontline too, and it pays off on  the bottom line results

Jeff Frick:
Yeah. So just to kind of wrap it up, I just want to something you acknowledged  again in the talk you just had that this  is not easy and that,  you know, a lot of the tooling and  the Gen AI and all these things will take care of the, the mundane and the rote and the stupid stuff. But it's not going to take care of the hard stuff.

Brian Elliott:
That's right.

Jeff Frick:
So it really it’s freeing up time  for you to invest in this stuff that's  going to be hard and a little bit  more difficult

Jeff Frick:
That's right. And I'll tell you, one of the things that I've observed though is I think a lot of CEOs are under pressure, right. CEO turnover hit an  all time high last year. The board pressure, the market pressure is through the roof. Some of them and I've  been in this spot before are falling  back into what can kind of feel comfortable, which is you're trained  to have all the answers. Right, right So you start giving out commands and having all the answers. It’s hard but  part of this is how do I think  about this as I can still set those  big aspirational goals, but I can say, I need all of you to figure out how we're going to get there. I'm going to enlist you in doing this. And by the way, the reward is you'll learn to  your career is going to grow and go additional places  by doing that. But as the leader, you got to  think about this as not just do I have all the answers, but how does my team  have to have the answers to drive the the objectives that we've got?

Jeff Frick:
Right.  I just love it. It just keeps coming back to team, team, team. Because that's Yeah that's the unit where stuff gets accomplished, right? Individuals contribute but it’s really the teams that move everything along.

Brian Elliott:
That's right. I mean what gets automated is things that are rote, individual tasks. What remains  is complex. It's hard. It's creative, it's interdisciplinary in nature. That's why more  than ever, actually, human centered leadership is going to be a much better answer than falling back into I've got all the answers and I'm the boss.

Jeff Frick:
You keep sharing the answers Brian on Work Forward And we’ll  keep subscribing cause you've got so much  great content in those things And I love all  the use cases.

Brian Elliott:
Thanks Jeff

Jeff Frick:
And it’s not just 1 or 2 companies, as you showed  on that slide. There were dozens and  dozens of companies that are  adopting this. If you're not, there may be a slot a logo on that slide (for) of one of your competitors

Brian Elliott:
Exactly, exactly. Somebody in your industry most certainly is.

Jeff Frick:
All right Brian well it was great to catch up again as always. And thanks for time.

Brian Elliott:
Thanks, Jeff. Appreciate it.

Jeff Frick:
All right. He's Brian  I’m Jeff. You’re watching Work 20XX Special Edition coming from Running Remote in Austin, Texas. Thanks for  watching. Thank you listening  on the podcast Catch you next time take care.

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Brian Elliott v3: Invest, J-Curve, Goals, Team | Work 20XX podcast with Jeff Frick Ep43 from Running Remote 2025, Austin, TX

English Transcript

© Copyright 2025 Menlo Creek Media, llc.