Shay Howe and Darby Frey believe the path to better management starts with a question. Howe, former VP of product at Belly, and Frey, former head of engineering at Belly (both recently left Belly for new, undisclosed jobs starting in 2017) just launched Lead Honestly, a weekly email product that sends managers five questions, and one management tip, per week. The service is aimed at creating better communication and trust between managers and employees, particularly as employees transition into leadership roles, which require a new skillset that can be tough to learn on the job.
“Some companies are great about training these new managers and helping them develop the skills they need to be successful,” Howe wrote in a Medium post announcing the product. “Sadly though, most companies don’t offer any training or mentorship, and new managers are left on their own to figure out right from wrong, good from bad.”
Lead Honestly addresses this through weekly emails with questions that start conversations around some of the trickiest management challenges, designed to be asked during a manager-employee one-on-one. Howe offered the following examples:
- What keeps you engaged?
- What is your largest frustration?
- What is something you would like to try?
- Who deserves more recognition?
- Where may I help you?
The email also includes a management tip to help guide conversation: “For insight into someone’s thought process and interests, ask them to ‘please say that one more time.’ Their answer will provide a new explanation with different context.”
They’re creating the questions based off their own experience, research on management, and discussions with leaders in their community. Each of the five questions deals with a different management challenge, and they’re internally tagging questions so in the future they can offer managers a one-stop-shop for questions pertaining to a certain area (such as retention, happiness, and productivity). They also plan on building an FAQ that offers additional support to help managers turn feedback into actionable insights. Subscription to their service costs $9 per month.
While it’s a side project for the two managers, it’s a concept they’ve long pondered over years of working in technical management roles across Chicago. Howe noted that managers are usually promoted to their position after making exceptional individual contributions, but that doesn’t necessarily prepare them for the unique responsibilities of managing a team, such as building trust, retaining employees and maintaining productivity. For Howe and Frey, one-on-one meetings were often the best way to gain trust and get insight to these challenges, but they had to learn over time the best way to spark meaningful conversation.
Though an email product may seem bare bones for now, Howe said they wanted to keep it simple so it could easily fit into a manager’s workflow.
“I wanted something that was really easy, the barrier to entry is really low,” he told Chicago Inno. “There’s a handful of great products that do things that are similar to this, but they do a lot more…I want advice, questions, and how do I integrate that into the workflow I already have? Email being the most simplistic way to get that started.”
The duo have tested the product with leaders in their network, including a managing director at Prota Ventures where Howe is a partner, and they put Lead Honestly on Product Hunt earlier this week. Howe declined to share user numbers, given the early stage of the product, but he said early feedback has been promising.
“It’s to help people become better leaders,” Howe said. “This seems like the best lightweight, easiest way to do that.”