Executive onboarding: The framework for balancing support and autonomy


Next week, I’m onboarding a new senior team member at HousingWire. This new leader will be taking over a function that I’ve been leading for quite awhile. I’m excited for the new energy, creativity and skills, and I’m giving a lot of thought on how to set up a new manager for success. 

Through the lens of a CEO or founder, transitioning responsibilities to new executives and team members is a required element of growth. By necessity, we’ve all worn multiple hats and led different functions in the growth curve of our companies, but there comes a time when hiring the pro and passing the reins is required to unlock process (and bandwidth). 

This is a timely topic in my business, as well as in the mortgage and real estate markets. In the past month, HousingWire has covered nearly 30 “People Movers” of note. These include big hires like Rick Roque joining Sierra Pacific Mortgage, Peter Knag taking the CFO seat at OfferPad, and Planet Home Lending recruiting Bill Shuler to the CIO seat.

The velocity of these executive hires and changes signal that owners, executives and managers have their eyes on the horizon and are getting prepared with the necessary talent to push their businesses forward. 

To prepare for this hire, I spent time thinking through practices learned from my own experience and took to LinkedIn to gain perspective from industry executives.  Here’s the executive summary takeaways: 

  • Onboarding a new executive is a delicate balance of providing support and granting autonomy.
  • Experienced leaders emphasize the importance of balancing guidance with the freedom to innovate, ensuring that new executives are empowered to make changes and lead their team.
  • By clearly communicating expectations, fostering trust and encouraging independent decision making, you can set the stage for a successful transition.

Here is the full framework for setting up new leaders for success. As CEO, I know that successfully communicating and executing this framework will set my new team member up for success and also make them a better leader for their own team. 

1. Establish clear expectations and vision

Setting the stage for success begins with clearly articulating the company’s vision, values and strategic goals.

Kent Nies, founder of White Stag Ventures, emphasizes the importance of communicating the company’s culture and foundational pathways for individual growth and development. He advises: “Articulate the company’s culture — its values, vision, and foundational pathways for individual growth and development. Introduce and offer access to key personnel, applicable data and systems, and best practices with the goal of empowering the new team member right from the start.” 

2. Empower through trust and autonomy

A recurring theme in the advice from leaders like Phillip Cantrell and Kelly Yale is the importance of stepping back and allowing the new executive to make their mark. 

As Cantrell succinctly puts it: “… get out of the way. The CEO role, yours, is to set the plan in place, then provide the resources for its achievement. Not to micromanage. (Said the pot to the kettle).” 

Providing the resources needed for success without micromanaging fosters a sense of trust and autonomy. Yale adds: “Let them take to the team without you, learn the ropes honestly, and be encouraged to have a true voice.”

3. Thoughtful introductions and integration

George Milian, former senior vice president at Rocket Mortgage who is now the founder and chief strategy officer at Steps After Life, offers a detailed framework for onboarding that includes proper introductions to the team, adding the new executive to group communications and providing company swag to create a sense of belonging. Here is a screengrab from a recent LinkedIn comment: 

4. Mentorship and continuous support

Mentorship plays a critical role in onboarding, providing the new executive with guidance, insight and support as they navigate their new role. Nies highlights the value of acting as a mentor to offer ongoing support. “Act on the notion of mentorship — which will bring guidance, insight, and support as they navigate the new role,” he advises.

Regular check-ins and an open-door policy can ensure that the new executive feels supported without feeling micromanaged.

For certain roles, mentorship may mean providing examples of brand and executive voice so new hires can hit the ground running. Alyson Austin, principal and co-founder of Gaffney Austin, suggests, “Share all files with them to get a feel for your persona so they can match your tone.” 

5. Create opportunities for feedback and reflection

Providing space for the new executive to be creative and form their own opinions during the first few weeks is essential. Mike Cush, a 25-year veteran in the mortgage industry, recommends, “Give them a few weeks with no guidance or guardrails other than to get acquainted with the people and the opportunities. Freedom to learn and form their own opinions. Then start talking strategy.” 

Documentation can be really helpful for reflection and feedback loops. Documenting observations and learnings during the first 30 days can offer valuable insights into potential improvements and ensure that fresh perspectives and first-impressions are shared. As a CEO, I’m always eager for a fresh set of eyes and to hear first impressions. 

6. Facilitate team bonding

Building strong relationships within the executive team is critical for long-term success. Scheduling informal gatherings, such as dinners, within the first 48 to 72 hours, as suggested by Milian, can help the new executive bond with their colleagues in a relaxed setting. This fosters camaraderie and enhances team cohesion.

7. Balance freedom and guidance

Finally, it’s crucial to strike a balance between freedom and guidance. Encouraging independent decision making builds confidence and initiative. I aim to demonstrate trust in the new executive’s ability to make decisions and support a leadership culture of confidence and autonomy. This approach is meant to help new leaders grow into their role more effectively and cultivate a proactive mindset.

Jeremy Dean, co-founder of Elite Title Company, advises against completely stepping back, highlighting the importance of staying available and communicating the company’s vision clearly.

“You don’t just want to hand them the keys and get completely out of the way. … There’s a difference between throwing someone in the deep end and running off, and throwing someone in the deep end and making sure they see you and hear you,” Dean said. Success is found in the balance. 

Wrapping this up — as I onboard new team members and executives — finding the right balance of providing support and granting autonomy is the top priority. This starts with clearly communicating expectations, fostering trust, integrating the new leader into the team, offering mentorship and encouraging independent decision making. The tone set on day one will influence the tone for the entire working relationship. 



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