Imagine this: being so meticulous in your candidate screening process invites an unexpected face-to-face investigation from Federal Agents. That is what our special guest, Lee Ann Howard, had to go through when starting as a recruiter in her early 20s. The secret to her 'suspicious' expertise? Simply asking the right questions and listening carefully to candidates.

Lee Ann is the visionary Founder of Howard & O'Brien Executive Search. With a keen eye for identifying top talent in senior management roles and a specialization in HR, finance, and sales and marketing functions, Lee Ann stands as a beacon of excellence in the realm of executive search.

You will surely enjoy Lee Ann’s insights on how to build a continuous pipeline of senior management roles for your clients and what it takes to have long-lasting strategic client relationships.

Episode Outline and Highlights

01:18 How Lee Ann left broadcasting to get into recruitment.
05:05 What made Lee Ann stand out in her early years; Her astonishing story of why she had to be investigated by the government because of her recruitment activities.
12:05 Emphasizing learning and development.
20:04 From corporate to executive search - Lee Ann shares her transition.
27:15 Discussion on the board recruiting business model of Howard & O’Brien.
45:48 Lee Ann explains their Conversation with the Board program.
48:38 Discussion on their Reverse Placement program.
51:17 How to cultivate long-term strategic client relationships.
57:30 Making it a family business - how Lee Ann’s children eventually joined her in the business.

Unexpected Government Investigation for Doing a Thorough Job

Lee Ann shared an astonishing story about being investigated by federal agents because of their extensive knowledge of security-cleared roles and positions.

“I ended up getting investigated by the government because they thought I was a spy because I knew too much … I literally got visited. I was visited by the government. It was unbelievable because I was sitting in my office and the receptionist came back and they said, there's somebody here from the government to see you. And I'm like, I've paid my taxes because that's the only thing I thought I could possibly do wrong. And I got taken into a conference room and they said, we believe you know too much about what's happening. And I'm like, no, I'm not a spy. I don't work for Russia.”

This made her realize that she was probably doing something right if she was getting information that other people were not getting in their industry. Indeed she was! Asking the right questions, and being meticulous in her job, contributed highly in her success as a recruiter and later on as a recruitment business owner. Some of the takeaways on Lee Ann’s success factors are as follows:

Instinctive Recruiting Ability
Curiosity and Continuous Learning
Strong Relationship Building
Commitment to Hard Work
Personalized Approach
Client and Candidate Engagement
Being Not Focused on Sales, But on Relationships

Which of the above success factors resonate most with you as a recruiter or business owner?

Board Recruiting, Conversation with the Board, and Reverse Placement Programs

Lee Ann also discussed key strategies that they implement in Howard & O’Brien with the focus of providing a continuous stream of C-level talents to their clients. The three main programs she discussed are Board Recruiting, Conversation with the Board, and Reverse Placement. Below are the key concepts of the programs:

Board Recruiting

Board recruiting is the process of identifying and placing individuals in board positions for organizations. Unlike traditional executive search, it involves adding responsibilities rather than replacing someone. The process includes:

Engaging with CEOs, board chairs, or governance committees to define the board’s needs.
Creating a strategic long-term plan for board composition.
Ensuring cultural fit and alignment with the company’s strategic direction.

Conversation with the Board

This is a program aimed at increasing diversity and exposing more candidates—particularly women—to board opportunities. It was developed as a way to help executives, who may not see themselves as board material, realize their potential for board service. It involves:

Facilitating networking opportunities between potential board members and current board leaders.
Encouraging companies to consider non-traditional candidates who bring valuable perspectives.

Reverse Placement Programs

This is a specialized career development service for executives looking to join boards. It is either funded by companies or individuals and serves as a way for leaders to continue their professional growth. It provides:

Guidance on positioning oneself for board roles.
Strategic networking with board leaders.

These programs put Lee Ann’s team in a strategic position, providing them a long-term relationship-building with existing clients.

Cultivating Long-Term Strategic Relationships

On this topic, Lee Ann summarized what can make you stand out with the following experience she had: “What makes you different is what you're trying to do. And I think it's the little things. There was a marketing person that I was interviewing for a job and she knew I'd just gotten a new puppy and she sent me this little assortment of stuff for my puppy. Now I still remember that because, I mean, she listened to what I was saying. It, you know, she probably spent $20 on it. But what an impact.”

It is indeed the little things you do. Some of the best practices that Lee Ann and her team have been doing over the years are as follows:

Long-Term Value Over Transactions – They prioritize relationships rather than quick sales, consistently providing valuable insights, industry articles, and strategic advice.

Community Engagement – Each team member is involved in community initiatives, reinforcing their reputation as good corporate stewards and deepening trust with clients.

Personalized Touchpoints – They maintain relationships through handwritten thank-you notes, customized gifts (e.g., olive oil or cherry salsa), and small but meaningful gestures that make an impact.

Being Helpful Beyond Business – They go beyond recruitment by assisting clients in unexpected ways, like recommending a plumber and reinforcing their role as trusted advisors.

Their approach is centered on authenticity, generosity, and a long-term mindset, setting them apart from competitors. As Lee Ann concluded, “It is putting yourself second and putting others first.”

Lee Ann Howard Bio & Contact Info

As Founder and Chief Executive Officer of Howard & O’Brien, Lee Ann Howard brings with her a passion for understanding people and dedication to following their journey in executive leadership. In her 25 years of connecting high-caliber candidates with her clients, she has solidified her reputation in driving quantifiable success for million and billion-dollar companies across North America.

Lee Ann leads a Women-Owned Business and carries this spirit into diversity, inclusion, and equitable placement strategies.

Lee Ann founded Conversations with the Board® in 2001 and continues to lead workshops for those who serve or have the desire to serve boards. She is currently on the board of the American Heart Association as Leadership Development Co-chair and past Board Chair as well as Case Western Reserve University (CWRU) Family Business Center Advisory Committee. She has served on the boards of MetroHealth Foundation Board - Membership Committee Chair; the John Carroll University Entrepreneur Association - Executive Committee; In Counsel with Women - Membership Chair, The Gathering Place, Women’s Community Foundation, and Business Volunteers Unlimited (BVU).

Lee Ann is especially passionate about and involved in the shared impact of individuals in greater Cleveland. Over the course of her career, she has received the National Association of Women Business Owners Top Ten Award in Northeast Ohio...