How Careful Planners and “On-The-Go” Learners Can Work and Thrive Together

Leen Kawas
5 min readAug 29, 2023


While some learners appreciate the idea of preparation and planning, others have higher risk tolerance and are more than happy to dive right into any task and “learn by doing”. Both methodologies can be positively impactful in a professional setting, and can together be wildly successful. However, with such different approaches, methods and appetite to risk, how can these unique types of learners and workers complement each other? What can they do to maximize professional outcomes?

While they appear outwardly different, both workstyles do complement each other, with successful teams leveraging the strengths of each style to generate a symbiotic harmony. In fact, both of these styles often need each other to pick up where the other falls short, creating a well-balanced partnership. In practice, “planners” need the “on-the-go” professionals in order to progress, while “on-the-go” professionals need “planners” in order to build a strong foundation so they can pursue their breakthrough ideas.

Who is a Classic Planner?

Thriving on strategy and organization, planners often operate within a well-organized space, carefully develop plans, and excel within structured parameters. They’re often careful and consider every angle of a prospective problem before implementing solutions, ready for any occurrence and outcome. These classic planners often arm themselves with extensive “to-do” lists and bask in the idea of crossing off accomplished tasks.

How Do Classic Planners Succeed?

Preparation is often key. Thus, preparing for various outcomes and planning the next steps can often elicit many benefits. Foremost, this cost/benefit analysis and readiness plan provides a template for the various steps that may be needed within a project. Having such a detailed roadmap may make stakeholders, team members, customers and investors feel confident about a product, project or an organization as a whole.

Where Does the Classic Planner Fall?

While a comprehensive plan can provide many benefits, this exhaustive plan can slow down processes, or inhibit “out of the box” thinking. Overplanning may also inhibit the Classic Planner from making a decision and pulling the proverbial trigger on an action plan. It is important to appreciate that even with the best plans businesses are typically not fully predictable, and being flexible with the details of the plan is critical to assure successes and appropriate progress.

“Learning by Doing”, a complimentary mindset to careful planners

The “learning by doing” methodology is the antithesis of the classic planner methodology. Sometimes referred to as “experiential learning” this type of learner relies on “actionable doing” to gain an understanding of a particular concept.

Aristotle, the ancient Greek scientist, and philosopher, put the “learning by doing” methodology into more eloquent terms. “For the things we have to learn before we can do them, we learn by doing them.”

Benefits of the “Learning by Doing” Methodology

Many effective entrepreneurs are learners by doing. In fact, various scholarly articles and analyses support the idea that entrepreneurs and leaders tend to be “on the go” learners, whilst professional academics and individuals within roles that support finance, accounting and project management tend to be “planners”. Many entrepreneurs and leaders embody the following traits:

A Satisfying Personal Accomplishment

The “learning by doing” methodology is, by definition, a hands-on undertaking. Although individuals may first receive some basic instruction, they often boldly forge ahead with little direction from others. Whether they accomplish their goal with few roadblocks or make mistakes but keep going, they’re likely to feel a sense of personal accomplishment afterward.

A Truly Memorable Experience

When an individual is compelled to perform a skill while learning it, they’re more likely to internalize that experience. This personalized learning shows the value of this approach and helps to provide motivation to move forward.

A Career Growth Catalyst

I believe “learning by doing” methodology fosters an open mind and a “can do” attitude. This positive mindset can set the stage for further career development. Examples may include team leadership and promotional opportunities.

Where the “Learning by Doing” Methogolody May Fall Short

The “learning by doing” methodology carries two significant downsides. First, if an individual teaches themselves to perform a task or solve a problem, they may not follow the exact same sequence every time. Even if they manage to duplicate the process, their method may not be the optimal way to achieve the desired result.

Equally importantly, the “learners by doing” may not be as prepared with risk mitigation plans or might underestimate risks. And while they are able to articulate the vision and mission in a clear way they might fall short in communicating the details that enables them to communicate effectively with their team members.

Leveraging the Strength of Both Workstyles

More often than not, employees with two opposing workstyles must find a way to work together. To maximize outcomes, both types of workstyles need to come together to leverage the benefits of their unique learning styles to the benefit of the overall project. As an entrepreneur and a learner by doing, I extremely appreciate partners and team members that are classic planners. What has been a breakthrough for me in my career is finding a way to communicate corporate or business goals while at the same time having a keen ear to what a classic planner has to say so we as a team can move forward with clear timelines, budgets and risk mitigation plans. Ways you can support both styles to thrive in your organization:

For the Classic Planner

  • Where possible, encourage planners to organize and manage their own projects. This includes setting goals and objectives along with establishing applicable deadlines.
  • Seek ways for planners to have uninterrupted time to complete key tasks.
  • Support planners in “thinking out of the box” to find innovative solutions that address workplace challenges.

For the “Learner by Doing”

  • Provide “on-the-job” learners with sufficient information and time to make a well-thought decision or complete a project.
  • Structure a project so that “on the job” learners can use their creativity to accomplish a preset goal while perhaps discovering a better way to achieve the outcome.
  • Although focusing on the process is important, meeting deadlines is key to accomplishing goals. Provide guidance on helping “on the job” learners to set and adhere to applicable deadlines.