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The Most Bang for your Leadership Development Buck

Updated: Jan 29, 2023

What if I told you for less than $500 per person, I could offer you a learning & development experience that would drive engagement, provide leadership development and build business acumen in eight hours. Would you buy?


Bam! I would! I don't know about your budget, but making the most of limited training & development dollars is a priority.

For 10 years, my team developed and produced an annual leadership conference for Southwest Airlines. It was such a rewarding project and one that we loved. We hosted speakers such as Ken Blanchard, Patrick Lencioni, Jim Collins, Brené Brown, Lou Holtz and Peyton Manning. Oh, and karaoke with 800 participants, skits, fashion shows, group yoga, comedians, live bands. We did it all - developed the content and produced the day. Dang, but I was proud of the Leadership Summit Team.



The content of the Leadership Summit targeted developing senior leaders. It took the place of one of our quarterly business updates for the Director and above group. Here’s where the bang for your buck comes in: We used the other 500+ seats for leaders at manager and supervisory levels across the organization. It was a terrific way to help our front-line and mid-level managers tap into a conference-style day of development and stretch their thinking to the next level of leadership.

The Benefits of Getting Leadership Together

The concept of an internal leadership conference began with a leadership learning day hosted onsite at Southwest's University for People. It became apparent that leaders were hungry for development and the team developed a conference style day. That year I had the opportunity to attend as a participant and marveled at the feat to pull off a fantastic day of learning + business updates + pep rally. The 10 years following I had the privilege of leading the Leadership Summit Team.

The conference began with an audience of 700 in 2010, and we targeted a slight increase in audience size each year. In 2019, we hosted 1,000 leaders at an in-person conference. 2020 Leadership Summit went virtual and we extended our reach to all leaders at Southwest – 5,000+ Supervisors and above distributed across airports in the United States. Bam.

Scale Creates a Huge Cost Benefit for Leadership Development Conferences

The first benefit I hope you're seeing is the cost benefit of scale. Getting top quality, engaging content to as many participants as possible makes sense. Yes, it would have been more than worthwhile to invest in the 250 senior leaders across Southwest. It’s even better to spread that cost across a larger audience of leaders, thus realizing smart financial spend and increasing the engagement and skillset of a larger leadership audience. Leadership Summit budgets included leading thought leaders and excellent venues, at under $500 per participant. I would argue that really, a fully loaded cost below $500 a head (lodging & meals included) is cheap. You can't find external leadership conferences for less than that.

Don't Forget the Business Value of Employee Engagement at a Leadership Conference

Another benefit I'd like to note is the sharp increase in engagement you realize from an opportunity like this. The agenda for Leadership Summit was a strategic mix of business update, leadership development and culture infusion. We heard from the CEO, CFO, COO, all the C's, about key initiatives, strategic priorities, progress against goals and so forth. The audience left with a solid grounding on how the business was doing. The goal was to increase business acumen and provide key points leaders were expected to communicate to their teams.

An infusion in Southwest's culture and appreciation was another key objective for the program. One year we hosted a fashion show to highlight the new Crew uniforms – that was cool for participants and the Crew uniform team (assessing, selecting, testing and finalizing crew uniforms is no small feat). Another year we developed a video of employees across the system appreciating their leaders. We brought in comedians and live bands. We had fun and enjoyed being together. Conferences are 100% about business. They can also be a way to appreciate and remind leaders that we are all in this work together.


“This was THE best Leadership Summit to date! The speakers were phenomenal and really left me inspired, energized and prepared for the rest of this year! Thank you for an incredible day of training!” - Southwest Airlines Leader

Stretch the Dollar with Follow-up Learning & Development Activities

We’ve found that leaders were jazzed after the conference. They started book clubs for their teams, were eager to debrief video from the event, and generally, kept talking about the content for a while. We also planned "Leader Chats” for folks who were not able to attend. We might show the Lencioni portion of the conference, for example, and host a debrief following. Stretch that dollar and the learning opportunity.

Develop Leadership Storytelling and Speaking Skills

Another perk of hosting an internal leadership development conference is the value you see in developing leaders as storytellers. In 2015, we introduced a concept called "SWA Talks" modeled after TED Talks. Presentations were 20 minutes with a crisp message and few slides. SWA Talks became an incredible development experience for up-and-coming senior leaders, and the audience loved them. We had leaders reaching out to see if they could develop a SWA Talk. And let's talk scale again: we recorded SWA Talks and hosted most of them on our learning management system for employees to view. Popular topics included diversity & inclusion, cyber security and the economics of a flight. All included personal leadership stories. Bam. Development for one is development for all.


How to Develop a Leadership Conference for Your Company

Producing a leadership development conference is no small feat. It's 100% teamwork + 50% we will figure this out!

Let me share with you a few things to consider that made a difference in our production efforts.

Build a Core Production Team to Develop and Run the Leadership Conference Day

Build a core crew who gets the hang of things and are assigned to the program each year. A maniac (maniac on a relentless pursuit for perfection, in a positive way) running the A/V crew helps. This is a shoutout to you, Brittany Bellair.

The Production Team was a cross-collaborative effort across the People Department and Southwest Airlines University. We included a team member from Communications in latter years. We sought out folks who had a passion for leadership development and wanted a rewarding development project.

Some years the agendas fell together with perfection. Other years we manhandled the whole day. Every year was a success and hearing about the impact of the day afterwards was a joy.


Get Department Heads Invested in Developing Their Leaders

Assign an allotment to each department and have them choose who will attend with some general guidance about how to use the allotments (recognition, engagement, retention, stretching, etc.).


Start Your Leadership Conference Planning Efforts Early

We hosted the conference in late summer or fall, per the timing that worked best for our business. Figure out that optimal timeframe when your business has a pause and will allow a majority to attend.


Logistical planning for the day should begin no later than 6 months out. Begin working on the agenda, speakers and theme for the day at least 9 months in advance. You'll need that time to explore concepts and core messaging with senior leadership, propose and vet the availability of speakers and begin to get internal speakers prepared.


Two tools that will help you keep production efforts and the conference day organized:

  • A timeline of key events to which the conference team will be managing. We used a PowerPoint slide at one point for a timeline view at a glance. We used Excel in later years to also track owners and other key dates as the production team grew.

  • A detailed agenda. Make that a very detailed agenda starting with the preparation and set-up day through the follow-up activites that need to take place. This agenda showed who and what needed to be where and by when. It was the common document we all used to be in the know and track the day. I'm sure this was an irritating document to complete for the team; it was an invaluable tool from my perspective. Plus, the detail came in handy when we wanted to refer to previous years.


Mine Leadership Conference Survey Feedback Like Gold

At the conclusion of each conference, we sent out a survey with the request for genuine feedback. And boy, did we receive feedback - of all tenors and varieties. We knew the year was a slam-dunk when the worst feedback we received was about the temperature of the catering. Feedback gave us valuable intel on formats that worked best for our leadership team. For example, the first year of the conference included a selection of breakout sessions. Via the feedback survey we learned that participants preferred a main plenary session all day.


We learned all kinds of things:

  • When it was time to adjust the live music selections

  • When table decorations and settings were helpful or annoying

  • The topics that leaders most valued

  • How much networking was just right to balance the day

  • Which venues and meal options created an environment conducive to the purpose of the day

  • When it was time to spice up the agenda and learning formats

We poured through every detail of the survey like it was gold. And it was. Even though survey feedback remained at a high of 4.5 - 4.9 (5.0 scale) each year, we read through every comment and weighed the input on every speaker and section of the day to see how we might improve the following year's conference. I believe that because we took input to heart and incorporated suggestions, leaders were proactive about survey responses.


Leadership Development Conferences That You Host are a Win

I look back at Leadership Summit as a favorite project and a leading strategy to develop leaders, reinforce business objectives, and share a consistent leadership message. It's also an excellent infusion of culture that gives leaders the pep to keep going strong.


We measured our success for Leadership Summit against the quality of external leadership conferences, and I'm proud to say that each year was a slam-dunk. Our feedback and net promoter-type recommendations were as good as or better than external options.


As a way to stretch your leadership development investment, a leadership conference falls high on my list of recommendations.


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