The Charter Workplace Summit Recap
4 Takeaways From Innovative Leaders Truly at The Edge of Work
In October, I was able to attend the Charter Workplace Summit, which brought together talent & people leaders in New York for a one day event to talk about all things work.
If you’re not familiar with Charter Works, they are a future of work media & advisory company that produces a great newsletter on the future of work (You can subscribe here) as well as premium advisory & research products.
I have been a subscriber since the launch, and have enjoyed reading their work as I find it fits within my wheelhouse of being pragmatic, practical, and progressive in how they think about evolving the workplace.
Erica Keswin Kicks off the Summit with a reading of her book The Retention Revolution
The event featured a number of panel sessions as well as some smaller group breakouts throughout the day-long event. While there were about 150-200 people it felt like a lot of familiar faces in the future of work & talent space. A highlight for me was meeting a bunch of people I interacted with online but had never met IRL. Another one was meeting 5 Edge of Work Podcast guests who were in attendance either speaking at the conference or attending as a guest.
If you are interested in seeing some of the content you can watch some of the recordings by signing up at this link (it’s free) but I wanted to give a brief overview of some of my highlights for the day.
#1 AI and The Future of Management
Jared Spataro (Corporate VP, Microsoft) has a fascinating job, and that is to work in ways with technology that are 18-24 months into the future and report back to us how it’s going.
As the GM For the Microsoft Co-Pilot products, part of Jared’s remit is to bake Co-Pilot into his role as a leader and to look for all the ways that it’s changing how he as a leader & manager leads to inform how the product is built and used. Doing this does two things. First, it opens the aperture of what work, and more specifically management, could look like, and second, it shines a lot where technology may fall short. But the view is interesting nonetheless. In his Q&A, Jared spoke about a number of his interesting observations on his own behavior as a manager and leader including:
Instead of starting his day staring down his inbox, he asks Co-Pilot to figure out the most important tasks, and then focuses on those
Instead of taking 90 minutes to review the decks and documents that are sent in a pre-read for a big meeting, He can use Co-Pilot to summarize them and get that done in 10 minutes
A couple other interesting observations that Jared made, that have the potential to change how we think about what work is, and who is doing the work:
Thinking and Listening in Meetings: It can be really hard to to think and listen at the same time. What if you could have a Co-Pilot do one of those for you in a meeting so you could focus on the other one? Would the action items and follow ups be more precise, thus making the meeting more productive?
It Feels like Having Extra Staff - Jared noted that having a Co-Pilot felt like having a “large staff” to tap on to get things done on command. An easy link to productivity gains.
We Need to Know More about “Work” - One key insight Jared had was that over time, he’s learned what to rely on his Co-Pilot to do and what he can do, and he delegates a lot more to his Co-Pilot than when he started. This means that we actually need to better understand why we are doing what we are doing at work, so that we can actually delegate things effectively, and for that matter, work on the right things.
Key Takeaways
Judgement Matters - Copilots (and perhaps AI broadly) is helpful at getting things done fast, but getting things done fast doesn’t always equate to getting things done right. Human judgment must be paired with any of these technologies to reap effective outcomes. In fact, Spataro suggested that judgment, delegation, and deep expertise were the most critical skills needed for managers in an AI driven world
Our Relationship with Technology - Jared noted that a big difference with this technology than prior ones is that it actually is going to change our relationship with the technology itself. It means rethinking how we engage with technology, from being something we ask for answers to being something we use to generate possibilities.
Expertise Still Matters - It’s true that AI tools can generate content and output really fast, in some cases, faster than humans. But if you want to get output that is both factually correct and novel, you need human expertise. This mirrors something that Ethan Mollick has also said before in his work with AI tools like Chat GPT. The broader and deeper you know on a topic, the more you can partner with an AI tool to come up with both better outputs and more novel outputs.
Managers Have a New Role - Spataro noted that skills like judgment, expertise, and delegation were critical skills in an AI driven world. These also happen to be skills that managers need in order to be effective managers. When asked if middle managers would continue to go away (like others have predicted) Spataro suggested that they actually are even more important. He cited Microsoft’s own approach to their managers (Model, Coach Care…check out my podcast episode with Joe Whittinghill for more behind this) as an example of what good management looks like in an AI driven world.
2) Iterating and Innovating with Company Culture in Hybrid and Remote Work
It’s hard to talk about the future of work without a conversation on remote and hybrid work. To headline this topic, Cari Nazeer (Charter) moderated a panel featuring Kausik Rajgopal (EVP, People, Paypal) and Tia Silas (CHRO, Shopify)
Kausik started the discussion by framing his definition of culture as the implicit software that we carry around in our heads when we show up for work. Traditionally, many thought of culture as something that you can only build in an office or together, but COVID has shifted that stance.
To build culture at Paypal, Kausik hit on the importance of ensuring that you’re anchoring whatever you are deciding back into the values and overall mission of the company. While it seems simple, it’s easy to miss in the rush to make decisions about where to work, policies, etc.
For Paypal, that means about 2 days a week in their offices, and when in the office a focus on also providing opportunities for employees to spend time in the communities, volunteering as well as meeting with customers. They also implemented a rule to start meetings 5 minutes past the hour or half hour to be able to provide margin time and breaks so people don’t burn out jumping from meeting to meeting. A big theme for this was around being intentional, testing, and then learning and iterating
Tia and her team at Shopify shared a similar sentiment of being intentional and aligning your decisions, policies and actions to your values of the company. Shopify is remote first, and has made their policies and decisions around this in very intentional ways. Tia mentioned how Shopify is a product that is for “crafters” and wants to be a company for crafters, and what that translates into is giving people the time as well as the space for crafting great work. For them, that translates into A) choice of where to work so that you can do your best work and B) having “Ports” where people can come together to “craft” and associate with one another.
A key strategy behind their work at Shopify was the idea of designing constraints to get people to think. One example of this was their famous experiment with canceling meetings in the entire company for 2 weeks. Tia shared a key lesson from this (outside of giving people back free time) was that it made people be much more thoughtful about the work that they were doing - if you wanted to schedule a meeting in that next 2 week window, you basically got a prompt asking you why you were scheduling the meeting. Too often, we get on autopilot with our norms and ways of working and do things without thinking about them. The meetings cancellation experiment was part of a strategy they call “controlled chaos” and while it was a shock to a system for many, it also caused people to think much more deeply about making smart decisions about how to do their best work.
Finally, Tia talked about this concept of “bursting,” which is intentionally bringing people together to solve problems, and using their “port” (offices) as a means to do that.
Key Takeaways
Intentionality - Both Shopify and Paypal seem to have thought about their strategy and decisions and made them in a very intentional way. There’s something to be said about focusing on designing conditions that enable people to do good work, and being able to do that in a thoughtful and strategic way is not easy.
Iteration - Kausik stressed the importance of what you start with doesn’t have to be what you end with, and the importance of listening and iterating based on what you learn. He said, “Never do a focus group in your head. You are not your employees!”
Don’t Forget “Why and “How” - So much of the remote/hybrid/office debate has focused on the where that we forget the other key elements of work design such as, why, how, who, and when. Both Paypal and Shopify seem to have picked up on this, which is evident in the robustness in their strategy
Finally, closing a quote from Tia that deeply resonated with me: “I used to think the future of work as something that would happen to me, but now I think that due to the rapid pace of change, it’s an opportunity for something that we can choose to create.”
3) Gathering as a Leadership Skill
In the afternoon, Massella Dukuly (Charter) interviewed Author and Facilitator Priya Parker (The Art of Gathering) about Gathering and bringing people together. As a fellow facilitator, I nerded out a bit during this session, and Priya had numerous great sound bites. Here were a few of my favorites:
Gathering is a Skill - “Gathering is a skill. It’s a learnable skill, and it happens to be the most important 21st century leadership skill.” Those were Priya’s words but I echo this. Tactically, knowing how, when, where, and why to run a gathering is critical, but from a strategy perspective, knowing when to use these can be a game changer for a leader in being able to achieve their goals
Building Trust - “ Trust is critical, trust isn’t just about the stump speech but the sprout speech.” Critical to any culture of an organization is trust, and it’s not just about the big moment, but rather, those everyday interactions (inclusive of gatherings) to build that trust the organization needs to thrive
Intentionality of Meetings: ”We need to get to a point where asking what is the purpose of the meeting is not taboo.” As much as gatherings matter, they don’t always need to happen. A sign of when gatherings are effective is when people can ask that question and it’s respected and acknowledged.
4) How People Leaders Can Lead During Constant Change
This session moderated by Kevin Delaney (Charter) featured three People & Business leaders in Cara Allamano (Chief People Officer, Lattice) Edith Cooper (Co-Founder, Medley) and Jelena Djordjevic (VP, People, Thumbtack)
At the core of this panel was the central question of - how do you lead your organization as a people leader in a world of continuous change? Whether it’s economic conditions, technology, changing employee expectations, or social unrest, it feels like executives (and employees) are dealing with change and shock and change in shock. SO how do leaders navigate this? While these are important questions for any executive, I appreciate how we had a panel of talent and people leaders who were there to respond to these questions. Since all of these questions and challenges involve people, having the HR/Talent/People Leaders answer them seems to be a sound decision.
My main takeaways from this panel is this: Having a strong, strategic and change-oriented people/HR executive is critical to enabling your organization and its people during times of difficulty and change. Here are a couple of examples of the things that each of these leaders shared that is worth noting:
Edith Cooper (Co-Founder, Medley)
Speaking Up on Social Issues - Edith noted how much more organizational leaders are being asked (and in return are stepping up) to tackle issues that impact their people and society. She also stressed that this was not going to dissipate, and that it is critical for leaders (and people/hr) to make sure that they are clear on their values and truly listen to diverse voices inside their organizations. She noted that in her time at Goldman after Eric Garner was killed, that there was a debate of whether or not to say something internally. She shared this to show just how much this has changed
Human Skills - Edith encouraged all leaders (especially people/hr) that soft skills are no longer nice to have, they are critical to leading in today’s world of work.
Jelena Djordjevic (VP People, Thumbtack)
Reactive vs Proactive - Jelena made an observation that one reason why companies may be struggling with all these changes is that they respond to them in a reactive manner. At Thumbtack, they have tried to really remain grounded in their decisions. “We optimize for values, and reason from first principles,”
Financial health AND People Health - Jelena noted that she saw her People teams role of being able to enable the success of the business through the success of our people. And just like companies use financial health to assess their business, they could also use that same rigor to assess their “people health.” For Thumbtack, that looks like OKRs for every single people leader, people scorecard, org health dashboards, held accountable to people outcomes (retention, engagement, attrition) - Her comment is one of the most simple, strategic and powerful ways to articulate the business value of the talent & people function
Cara Allamano (Chief People Officer, Lattice)
Hard times make for strong companies - Cara noted that despite how difficult times might be, many successful startups started during economic downturns.
Clear Eyes - At Lattice, Cara talked about how they had a value called “clear eyes,” which is all about fallibility risk - since we are human, we are not always going to be right, and things are not going to always work, and that’s okay. This is often a fear of many leaders. But this value around clear eyes means being honest about what’s really going on to be able to collaborate around solutions, versus hiding in fear around it.
Conclusion
Even though the event was only a day, I walked away with a ton of interesting takeaways and even more ideas from companies who are thinking and doing differently to create a better world of work. While there is a lot of work to be done, it was great to learn from some forward thinking leaders about what they are trying and doing to improve the workplace for their people. Special Thanks to the Charter Works team for putting on a great event!