One of the true joys of building Hello Generalist is the conversations with operators in our community. Take Joe. Looking at his resume, he’s clearly an operations pro having worked at some brands you may recognize like Lyft, Scale AI, and GoPuff. He’s been the Chief of Staff to the CEO at a 2 billion dollar company, did scheduling work in the Clinton White House, and lead ops inside a Series A fintech startup.
And today? Joe runs a therapy clinic. No, it’s not a fancy tech-enabled mental health startup. It’s a small business that gives back to his community. But thanks to the rise of fractional work, he’s still able to keep a hand in the tech world and support founders with his 15 years of experience — an incredible win-win for Joe, his community, and the startups that get to work with him.
In today’s issue, we explore managing cross-cultural teams, building feedback loops the right way, finding leaders in unexpected places, and how a Chief of Staff can support their CEO in ways no-one else can. Joe was a true delight to learn from — stay tuned for stories about an entire support team staffed by stand-up comics, how he taught Swedish engineers in their 20s how to use old school bank checks, and how he learned to dish the real feedback to his CEO. I know you’ll love learning from Joe just as I did. Enjoy! — Shaina
Drop 1. Navigating cross-cultural differences? Get your team in front of your customer
We’re a Swedish company with American customers. We had our engineering team in Sweden and our support team on the ground in New York. One of the things I noticed was there was a lack of familiarity with the customer and product from the engineering team.
It really is crucial to get all the areas of the company, all the way to engineering and those who aren’t customer-facing to get involved in using the product, in meeting the customer, in order to have that crucial, full-focus on the customer.
Take it back to your team:
- Does your company have employees and teams across state lines or even countries? Give them a single North Star to keep them aligned.
- It’s easy for engineering to lose sight of who’s using the product. Create opportunities for them to interact with your customers.
- Cross-cultural differences don’t have to derail your team. But it’s important to be aware of communication styles and work preferences and how they impact your team’s ability to work together.
Drop 2. Help engineers see what you see by showing customer problems, not just telling
One of the learnings that I have from establishing feedback loops between customer-facing employees and the engineering team is really identifying the biggest problems and prioritizing those problems.
What are the top 3 things that we could change in the app that would be the most crucial and would help the majority of our customers? This helps the engineers prioritize.
Take it back to your team:
- Joe implemented a weekly status meeting where they would collect customer support tickets and start categorizing them to help surface the top trends on what would best support customers.
- When collecting feedback from customer-facing teams, have them determine what are the 3 biggest blockers or changes engineering could make to help unblock the customer.
- Quantify and qualify the extent of your customer problem. A problem that has 50 tickets could be more important than the one with 5 tickets, but those 5 customers are still important. Help engineering decide how to focus their time.
Drop 3. Leaders can exist in untraditional employees
We had untraditional backgrounds on our team (our support staff were comedians and in theater). But I noticed some folks with leadership potential. So I gave some people tasks that were a little bit of a stretch. Or gave people an opportunity to volunteer for a project that I didn’t have time for. I started handing off work to people that I saw had talent and the drive to take on extra things.
These people didn’t have the perfect resume or experience but they were super talented and sort of athlete generalists that could take on leadership roles. And we promoted a couple of these folks into leadership roles.
Take it back to your team:
- When it comes to finding leaders in your company, don’t be afraid to look past the resume and experience. Look for drive and folks who step up to the plate.
- Provide ample opportunities for junior talent to showcase their initiative and take on more responsibility.
Drop 4. The Chief of Staff can be the critical thought-partner no one else wants to be
One big element of the role was being a thought partner and often providing feedback that nobody else would. Often you have folks that in a large company, want to work their way up and try to make a good impression on the CEO so they give positive feedback often.
I think part of my job was to give open and honest feedback, whether it was easy feedback or really challenging feedback that maybe the CEO doesn’t want to hear.
Take it back to your team:
- When bringing on a Chief of Staff, empower them to give the harsh feedback that you may not want to hear but need to in order to make yourself and the company better.
- Recognize that most of your direct reports want to keep you happy and may sugarcoat the truth. Leverage your Chief of Staff to find out what’s really happening on the ground.