Strategic Planning and Board Retreats – a recap from the 2019 Voluntary Bar Leaders Conference

On Saturday, July 13, 2019, I spoke at the 2019 Voluntary Bar Leaders Conference on the “Looking Out Into the Horizon: Strategic Planning and Board Retreats”. The purpose of the discussion was to help other attorney organization set the tone of their year with board retreats and strategic planning sessions. I spoke as the Immediate Past President of the Pinellas County Chapter of the Florida Association for Women Lawyers (“PFAWL”). Also on my panel was Amber Donley, Past President of the D.W. Perkins Bar Association and John Schifino, Immediate Past President of the Hillsborough County Bar Association. We discussed ways to engage leadership at a board retreat and the need for strategic planning sessions.



Most leadership organizations hold retreats to kick off the year and make significant planning decisions. You should include the entire board of directors or leadership team. Some organizations include spouses for a part of the event. Some organizations have the retreat at the organization’s headquarters while others choose an off-site location. Often times, your budget will determine your location.

The substance of the retreat should include a time for the leadership to get to know each other, whether that comes in the form of social time (lunch, dinner, etc) or in the form of an icebreaker. The decision must also be made as to whether the retreat should be formal or casual. PFAWL chooses a more casual retreat. DW Perkins and the Hillsborough Bar opted for more formal surroundings. Leadership should ways the pros and cons of budget, tone for the year, and what needs to be accomplished when deciding substance and style of the retreat.


Strategic Planning

Resources that you should utilize for strategic planning include your budget, your master calendar, information from previous events, and your organization’s staff. Your master calendar can assist in both assessing last year’s events for success in attendance and budget as well as planning for the upcoming year(s). Your organization should not fear doing something new or changing up previous events for better attendance. PFAWL stepped away from the traditional holiday cocktail party and in December 2018 held our annual holiday party at Pinellas Chocolate Company. Members were able to bring a guest and all attendees made their own chocolate bark, toured the factory, and were able to shop signature Pinellas Chocolate Company chocolate. The attendance was excellent and the buzz around the event continued throughout the year.

Every organization wants to operate within their budget and a retreat and strategic planning session will allow you to look back and forward long term. Leadership should be prepared to have an honest discussion as to which events brought in a surplus and which events operated in a deficit. That discussion may lead to other discussions about events, how to bring in a stronger surplus, and what caused the deficit in events.

By assessing previous events, your organization can grow. PFAWL’s signature membership drive event reached capacity. The committee looked at whether the event should be changed or whether the event should be moved to another venue. By having a discussion about the previous events and the current challenges, we were able to speak with the venue about our challenges which resulted in expanded hours for our event and more employees at the venue to assist with our event – at no extra cost to us!

If you have staff from your organization, you want to make sure you include them as well. Not only can the staff help by coordinating the sessions, travel, meals, etc. they are also vital to the health of your organization. It is vital that everyone is on the same page and having leadership and staff together is the perfect time to do that. The Hillsborough Bar has a large staff and John Schifino discussed the ways that the staff assisted and participated in the strategic planning sessions. PFAWL and DW Perkins are membership-led and do not have staff to assist.


Mistakes to Avoid

The top three mistakes we discuss were:

  • Don’t overcrowd calendar
  • Don’t do everything on your own- Delegate!
  • Don’t be inflexible and rigid

It is easy to forget that leadership in your organization may be involved in other organizations. By the time you have one event and one board meeting, you have filled up the calendar of your leadership who have other events and possibly other board meetings to attend. Be careful not to put too much on your calendar which could also lead to burnout.

Delegate! As leaders we tend to have a hard time delegating tasks to others. You do not need to do everything yourself. If your organization has a staff, they could assist you by following up with a venue or a sponsor, saving you time and stress. Ask a newer member to assist you at the check in table. It is a relatively low-stress situation that will assist the new member in meeting everyone and feeling like they are helping the organization.

Leadership must learn to adapt. In Florida during hurricane season, we must learn to adapt. Be open to cancelling and moving events whether it is for a natural disaster, low attendance, or other issues. It is better to move the event and have it be successful than to force it to occur and suffer a financial loss. Your calendar must also be flexible. Look around at other bar associations. If PFAWL is trying to host a CLE on the same night as another organization’s Judicial reception, our attendance may suffer. But by being flexible and moving the CLE, members can attend both the judicial reception and the CLE.


Helpful tips for a successful year

As you go into your leadership year, these are the helpful tips our panel wanted to share:

  • Support chairs/motivate/ check-in
  • Year long projects/ goals or tasks to complete
  • Collaborate

May leaders in organizations our volunteers. This means they are doing this for free and sacrificing time working or with their families. It is important to support your leadership, motivate them, and check in with them. Check in to see how they are, not just how their event is going or if they are meeting their deadlines.

Considering setting goals or breaking down larger events into tasks so that you can assist and measure if things are on track for a successful year. Want to double membership? If you measure that by tasks or by a year-long project, break the event into smaller pieces so that all leaders involved know what the criteria for success is. Update the leaders also with where they stand on their task/goal. If they need support, provide it. Unsure how to help, ask the leader. Jump in where you are needed.

Collaboration was a topic that we kept discussing during our panel. Collaboration is great for all organizations because we tend to all be fighting the same fight – more members, better programming, etc. PFAWL held a Pro Bono fair a few years ago. Our members wanted pro bono opportunities, but we didn’t have the ability to host an event on our own. We collaborated with the Fred Minnis Bar Association and brought in our three local legal aid societies to discuss what they were looking for. Members of Minnis and PFAWL were able to network with each other and learn more about the pro bono opportunities in our community. It was a great event.


Finally – Always say thank you. My favorite quote is “it is nice to be important; but it is important to be nice”. Sometimes all your leaders and volunteers are looking for is appreciate for a job well done, for their sacrifice, for their commitment and dedication. A “thank you” can go a long way.

Share Post

We accept credit cards, money orders, and cashier’s checks. For all credit card transactions, pursuant to The Rules Regulating The Florida Bar 4-1.5(h), Feher Law may charge clients the actual charge the credit plan imposes on the lawyer for the client’s transaction.