Ep 16: Hybrid Work F.A.I.L. Lessons: Top 50 Leader of MA Tiffany Mosher Taylor on Leading the Future of Work

In episode 16, I’m very excited to welcome Tiffany Mosher Taylor—recently recognized on the Top 50 Women Leaders of Massachusetts for 2024! Tiffany is a people resources executive and the current Head of People at Canoe Intelligence, a company redefining the future of alternative investments with cloud-based machine learning technology. Taylor’s extensive career spans heading up the people function at very noteworthy Boston companies such as Akamai, Aramark, Euro-Pro, Cengage Learning, dataxu, PatientPing, and Appcues.

Tiffany Taylor has more than 25 years of experience in HR leadership. She is passionate about providing strategic people consulting across the employee life cycle from recruit to retain to develop and people operations, and that's why she's joining us as a hero of hybrid work today.

Building Remote Connectivity for Employee Engagement

Tiffany explained that the leader's job has shifted in hybrid work situations, considering the current work environment. Remote work requires more intentional effort to build and maintain connections. She emphasized how important it is to focus on connectivity in a remote work environment. 

Tiffany shared that Canoe Intelligence is a remote first organization, so they make it a point to bring all of their employees together in person at least once a year, preferably at the start of the year so that they can align on business strategy and build relationships. She recommended a monthly focus on remote connectivity to keep engagement high in a remote work environment.

“A leader's job is to inspire, motivate, and create purpose for their team.” - Tiffany Taylor, Head of People at Canoe Intelligence

For example, Canoe Intelligence has two offerings for the month of June. These are not necessarily around business but around employee connectivity. There’s a Juneteenth event on June 18 and a pride event toward the end of the month to come together and learn. These are opportunities for employees to interact with others they may not normally engage with in their day-to-day work.

Tiffany's team is focused on remote connectivity with full support from the leadership team. Remote connectivity is important for emerging growth companies, especially with high rates of hiring. Building relationships and connections is key for employee engagement and productivity, as engaged employees are more productive.

Two Key Leadership Qualities for Adapting to Hybrid Work

We discussed the two important things Tiffany Taylor looks for in a leader: followership and learning enablement.

‍Followership: Would this person’s team follow them if they were to leave and take a job somewhere else?

‍Learning enablement: Does the leader provide a continual learning environment for their team?

Tiffany emphasized the importance of getting the team together in person if possible and carving out a budget for in-person team meetings. She gave a recent example of having a team off-site in Boston, which they ended by inviting the rest of the company employees that live in the Boston area to come together, get dinner, and go to a Red Sox game.

“I have weekly one-on-ones with my executive staff and my direct reports. I have biweekly skip meetings. I have monthly meetings with our senior leadership team, quarterly meetings with people avengers, and I leverage donut chat to the nth degree to just have random pairing one-on-ones.” - Tiffany Taylor, Head of People at Canoe Intelligence

Tiffany shared that all leaders need to create opportunities to build relationships and connections outside of work. When people worked in the office full-time, it was easier to overhear conversations between team members about shared interests and make connections that way. However, remote work makes it harder to check in with team members casually. In a hybrid work environment, connections are made by being intentional and putting effort into in-person gatherings.

Doubling Down on Your Company Values as a Tethering Force

Tiffany emphasized the importance of doubling down on your company values to build culture in a remote-first environment. She pointed to Christina Luconi, Chief People Officer at Rapid7, as a role model who has exemplified that work and how corporate values should not just be posters on the wall. It is crucial to align everything done within the company with its corporate values. Corporate values serve as a tethering force that keeps employees connected to the company's expectations

Tiffany explained that rewards and recognition should be given to employees who embody the company's values. It is acceptable to refresh company values if they no longer align with the mission, vision, or strategy. Company values should be integrated into performance management and promotion processes to highlight not just what employees can do, but how they do it. At Canoe Intelligence, company values are even incorporated into the interview process.

“We identify the right candidate for their skills and fit within not only being able to align with our culture, but help our culture thrive. We bring them on board with a very focused training on our values and then threading the needle through everything that we do from a people's perspective, rewards recognition, performance management, and promotion.” - Tiffany Taylor, Head of People at Canoe Intelligence

Managing Ambiguity in Crafting Hybrid Work Policies

Tiffany shared that Canoe Intelligence values having a remote first approach, but there are expectations around what that means. Setting clear expectations is important to help employees do their best work and reduce anxiety and biases related to remote work. Remote first does not mean traveling the world or working from coffee shops in different countries. Remote first offers flexibility by removing the commute but requires a proper workstation, high-speed internet, a secure and quiet location.

Tiffany shared that leaders should encourage open communication with team members.They can do that by setting clear expectations and holding employees accountable. She shared that leaders should manage ambiguity by being transparent and setting clear guidelines and policies. When communicating, try to provide as much context and seek feedback from employees to ensure clarity.

“I'm a transparent leader. I feel like it is my job to be transparent so that my folks have as much information as they can to do their jobs effectively. I never want anything to be ambiguous to my employees on my team or to those in the greater company.” - Tiffany Taylor, Head of People at Canoe Intelligence

Tiffany explained that while getting consensus from everyone is important, it’s even more crucial to balance consensus with what's best for the business. Her advice is to not rush communication and to over communicate rather than under communicate, as repetition is key for information to sink in. Finally, she recommended involving high potential employees in previewing communications and using a waterfall communication approach for feedback before finalizing communication. That way, you are empowering high performers by involving them in team communication and decision-making.

“There is no such thing as over communication. You have to remember that, on average, you need to hear something new seven times for it to sink in.” - Tiffany Taylor, Head of People at Canoe Intelligence

Hybrid Work F.A.I.L. Lessons: First Attempt In Learning

Tiffany shared the importance of learning from failures and mistakes, and using them as opportunities for growth. She shared that some of her greatest learnings came from falling flat on her face. She shared how important it is for leaders to demonstrate how to fail, learn from it, and pivot. Being authentic and accountable for when they mess up make them more approachable as leaders to their employees.

“Fail to me stands for: ‘first attempt in learning.’ Just own it, learn from it, and pivot. Sometimes it's more of a marathon versus a sprint, and you have to know when to sprint and when to jog.” - Tiffany Taylor, Head of People at Canoe Intelligence