Leadership Transition Tips from ThoughtExchange’s Chief People Officer

Dessalen Wood

6 minutes

Ideally, leadership transitions would be the result of months of careful planning. The new leader would be named while the existing leader was still in place, and there would be an amicable transition period where the handoff would occur. This new leader would go on to fit right in with the team and be off to a strong start.

In reality, changes in leadership are very rarely handled with the necessary foresight or resources. Once a decision has been made to bring in someone new, the myriad of complex issues that will result from the transition—everything from team politics to broken processes—are effectively left to this fresh new face to remedy quickly and efficiently, all while they attempt to set the company off on a new course.  

Effective leadership transitions are about more than just executive onboarding. It’s a high-stakes period in a company’s lifecycle that ought to be managed with care. As someone who’s handled many of these transitions myself, here are some of my tips for successful succession planning.

Remember that succession planning is complicated 

Harvard Business Review estimated that between a third and half of all new chief executives fail in their first 18 months. Some of this can be attributed to unrealistic expectations that lead to poor choices and lack of trust. 

Organizations would be wise to support new leaders in navigating the early periods of their career by helping them integrate with existing teams, build rapport with their peers, get a deep understanding for processes and operations, and get ingrained in the company’s culture.

Leadership onboarding programs tend to focus on bringing a new leader up to speed on processes and operational dynamics, providing them with detailed updates on ongoing projects and digging down into financial projections and goals. 

The problem with that approach is that it tends to narrow the leader’s focus from the very beginning, rather than giving them a breadth of understanding about the company as a whole. 

I’ve seen teams further reduce the new leader’s introduction to just their direct team. When that relationship is rushed or, worse yet, forced, you risk sacrificing the team’s health at a delicate time. Doing that will only pull the team’s focus away and cause an unproductive distraction.  

Questions new executives should ask themselves first
  • Who in the company has influence?
  • Who are my allies? 
  • Who is most fearful of change?
  • Are there any unhealthy biases that indicate a risk of resistance or stagnancy? 

These are all complex aspects of an organization that, if undisclosed, can be problematic for a new leader in their early months. Fortunately, employees and their HR partners can help bridge the gap between a new leader and the team. 

Communicate early and often 

Opening lines of candid communication between existing teams and new leaders during executive onboarding is often an early aspiration. Building that kind of rapport can be a difficult thing to do. 

Team members are often asked to speak freely to new leaders, with no certainty they won’t be judged for their honesty or the first impressions they create. Those who talk about dysfunction or concerns around strategy or goals are quickly labeled as negative, so why put themselves forward (even if this information may be critical to the new leader’s success)? 

It may be no surprise that we believe in good questions here at ThoughtExchange. Here are a few that new leaders may want to ask their teams to build trust and gain valuable insights into the department or organization’s health.

Questions new leaders need to ask their teams
  • What are some important things I should know about the team and our objectives in my role as leader?
  • What are some pressing and important projects/initiatives that need my attention in my first 90 days?
  • What do I need to know as a leader that will help me support the team and the business?

Cultivate psychological safety

The concept of remote work used to be a far-fetched “future of work” scenario for a lot of leaders, but as of spring of 2020, remote work and distributed teams have become an undeniable norm. 

Now that workers are no longer centralized in a single office location, leaders need new kinds of technologies that will help them make better sense of the mass amounts of unstructured information and conversations happening in the virtual working environment.

It doesn’t help that these conversations are scattered across the company’s tech stack: in emails, at online meetings, and in collaboration platforms. How are leaders supposed to get a full view of everything that’s going on when work is happening in so many different places?

One way of gaining trust while also getting to the truth of matters is to go to people directly and ask them questions. Don’t worry, I’m not suggesting that you go to individual people and ask them pointed questions about what you, as a new leader, should know about the company (although wouldn’t that be something?). 

There are technologies today (OK, I’ll stop being coy here, I mean ThoughtExchange) designed to help leaders have these kinds of vulnerable and insightful conversations with their staff, at scale.  

Top questions new leaders should ask for successful onboarding
  • What advice do you have for me to be successful as a leader in this organization?
  • What has gotten in the way of our success as a team? 
  • What are some things you would like to know about me, my leadership style or my experiences prior to this role?
  • What are some ways I support you in your role?

Get vital info; host an Exchange

The thing about ThoughtExchange is that when participants respond to questions, they do it anonymously. They can literally say anything that’s on their mind without fear of repercussion. For leaders, that means they get the raw, unfiltered, unvarnished truth. 

The anonymity on participants’ part also helps cultivate an atmosphere of psychological safety. Employees aren’t intimidated into withholding vital information. Such an approach allows an incoming leader the chance to ask their team about challenges they are having and of their honest expectations of their new leader. It’s also an opportunity for people to ask questions about the new leader’s experience and values in a safe way.

Opening up this two-way dialogue allows new leaders to gain a clear view of the field: where the problems are and what needs to be done to address them. 

Doing this quickly can allay fears and begin to build early trust and healthy working relationships within the team. With their opinions aired and concerns addressed, team members are more likely to adapt, abandon old habits and behaviors, and to support a leader who has demonstrated genuine curiosity and empathy as they transition into the company.

Most new leaders fail not because their skills or talents don’t match the role, but because they aren’t able to properly read the complex dynamics of their team members and their objectives. 

By interacting and engaging with existing team members sensitively, frequently, and candidly, leaders will ensure they have the best chance of integrating into the organization effectively and setting everyone—including themselves—up for success. 

About the Author

Dessalen Wood

Dessalen Wood is an innovative HR executive, seasoned speaker, and coach. She specializes in leading Learning and Development and Human Resources teams at some of North America’s most-respected organizations. In 2019 she left her role as Vice President, Talent Development at Cineplex Entertainment to join ThoughtExchange in the newly created role of Chief People Officer. Throughout her career, Dessalen has been passionate about creating work environments that bring out the very best in people. The connection to ThoughtExchange - the product and the team -was instant, and made the decision to join feel like a natural fit between like minds. Dessalen is based in Montreal with her husband, three children and her dog.