5 Painful Discussions That No Organization Should Ignore

This is the final in a 3-part series about Pain and Decision-Making.

Part 1 | Part 2 | Part 3

In previous posts, I described ways to see pain objectively, and how to identify pain points, and ways to fix them. In this article, we’ll be examining some difficult topics that most leaders tend to avoid.

The Painful Questions to Discuss

Now that we have reviewed what pain is and how to measure it, let’s examine how to self-evaluate yourself as a leader.

No matter what else is happening in your organization, there are 5 questions that can immediately reveal potential areas of vulnerability.

Here they are:

1. As leaders, where are our blind spots and biases?

Blind spots are areas of the field of vision that disappear. Unlike animals, human eyes are able to distinguish 100 different shades of color (BBC story by Adam Hadhazy)

But there are limits. Our perception can be easily skewed, causing us to collect the wrong data, interpret the data incorrectly, and make the wrong decisions.

Here are some ways to avoid this:


Frameworks, strategic and risk intelligence, innovation, communication
Grace LaConte’s basic framework of the 3 types of strategic intelligence


2. What do our customers/patients really want?

Often, we only hear only what we want to hear (Golden Rule) without considering what others want to receive (Platinum Rule).

Ask yourself:


feedback loop, healthy feedback, empathetic leaders, structured mechanisms
Components of a Healthy Feedback Loop in circle diagram



3. Are we doing a Post-Mortem review of every project?

A Post-Mortem Evaluation (also known as Lessons Learned) is a very helpful way to identify root causes and evaluate the areas of success & failure of a project, marketing campaign, or program.

It involves asking 4 questions:

    1. What happened?
    2. What went well?
    3. What did not go well? and
    4. How we can adjust for the future?

This simple but profound practice will allow you to gather information consistently, give everyone a voice, and use the conclusions to improve the next project.

4. How do our employees honestly feel about me as a leader?

Yep, this is a painful one.

Even when we offer an “open door policy” and encourage staff to tell us what’s on their minds, in reality the problem is not with our staff. It is with how we approach the situation.

When was the last time you actually looked at your company from the point of view of your staff?

Here are a few ways to do that.

  • Conduct an exam of any existing Corporate Ladder Bias. Take the time to identify your blind spots and any distorted perceptions as a leader. (Read What Happened When I Became an “Employee For a Day” and “Employee For a Day”: How to Start)
  • Take an inventory all existing methods of sharing feedback and bad news. You might use comment cards, anonymous tip line, 3rd party website, or other internal feedback loops.
  • Consider how many problems and concerns your staff feel too nervous to share with you. Trust me, this problem is present in even the most transparent organization.
  • Review your exit interview (or, as I call it, Offboarding) process; are employees invited to share the real reasons they are leaving? What happens with that information?
  • Determine whether your management philosophy includes participatory job design. This happens when leaders invite staff to participate in developing and evaluating their role in the organization’s long-term goals.
  • Recognize any signs of Frankenstein Management Syndrome. Signs that your company may be experiencing this include:
    • high turnover rates
    • an increase in sick days
    • staff arriving late and leaving early
    • sudden change in employee morale
    • low participation in company-sponsored events
    • sense of dissatisfaction and disengagement

5. Do we understand the struggles of our employees?

I believe most leaders find it very difficult to truly relate to their staff. It may even be a challenge to relate to customers (or clients or patients, depending on your profession). I call this condition Corporate Ladder Bias, and it’s something I have experienced myself while in different management roles.

Unfortunately, the majority of executive leaders do not take the time to truly experience what it’s like to work in the role of their Foundational Staff. Leaders who can empathize (experience the pain) of individuals at the bottom of the corporate ladder are able to build authenticity and trust. Without this connection, the leadership team is likely to lose credibility… and ultimately, control over the company’s ability to grow.

To overcome this blind spot, I challenge you to try something radical. For a full day (or several, if you are brave!), step into the shoes of your staff by experiencing their job just as they would do it.

  • Commit to seeing the company from their point of view.
  • Do everything that staff person would do.
  • Be open to learning from staff, rather than calling all the shots.
  • And prepare to learn a lot more than you bargained for.


organizational roles, leadership, organizational chart, foundational staff, executive managers
The Levels of Organizational Roles: Top Leaders, Management, and Foundational Staff


I call this process “Employee for a Day,” and it can be life-changing. Read my experience with it, and how to start it in your organization.

Examples of Leaders Who Ask Painful Questions

Signature HealthCARE, headquartered in Louisville Kentucky, did something radical. In 2011, President and CEO Joe Steier led his organization in a C-Suite to CNA program. Mr. Steier and his entire executive team completed CNA (Certified Nursing Assistant) training in order to better understand the challenges and frustrations of both the staff and their elderly residents.

Here is his description of what happened:

Signature HealthCARE is now listed as one of Inc 5000’Fastest Growing Private Companies. So obviously they’re doing something right!

Inc 5000, fastest growing companies, 2017 list, Signature Healthcare, healthcare Signature HealthCARE named one of Inc 5000’s Fastest Growing Companies in 2017

Thrive Labs founder Priya Parker and her husband Anand Giridharadas created a tradition called “I Am Here” days. Together, they decided to leave technology and to-do lists behind, and explore a part of New York City for a full day. Eventually, this turned into an open invitation for people to join their tech-free exploration and be “thickly present,” rather than distracted by less important details.

Read More:

If you decide to step into the world of your staff, consider that every single job role requires a unique set of skills. Even if their role seems basic, it might surprise you how much information your staff know (and what valuable insights they could share with you!)

To quote from the fabulous book Nickel and Dimed:

No job, no matter how lowly, is truly “unskilled.”
― Barbara EhrenreichNickel and Dimed: On (Not) Getting By in America

Nickel and Dimed, Barbara Ehrenreich, New York Times, New York Times Bestseller
The book cover of “Nickel and Dimed” by Barbara Ehrenreich


So now you know the 5 questions:

  1. As leaders, where are our blind spots and biases?
  2. What do our customers/patients really want?
  3. Are we reviewing “Lessons Learned” after every project?
  4. How do our employees honestly feel about me as a leader?
  5. Do we understand the struggles of our employees?

As an effective leader, you can examine the pain your staff and customers experience simply by hearing all feedback, even if it is unpleasant. Step into the discomfort by asking these questions. I think you will be amazed at the results.

To find out why we avoid pain and how to use it for intelligent decision-making, check out Part 1 and Part 2.


If you would like to discuss toxic problems in your organization, find out more here.


Grace LaConte is a business consultant, writer, workplace equity strategist, and the founder of LaConte Consulting. Her risk management tools are used around the globe, and she has successfully reversed toxic work environments for clients in the healthcare and non-profit fields. Grace specializes in lactation law compliance & policy development, reducing staff turnover after maternity leave, and creating a participatory work culture.

Find more at laconteconsulting.com, or connect with her on Instagram and Twitter @lacontestrategy.

Grace LaConte is a profitability expert, writer, and speaker. She is the founder of LaConte Consulting, which provides business owners with practical ways to improve their company's profit, growth, and value. Grace also shares her thoughts about marketing strategies and the dangers of predatory tactics used by MLM (multi-level marketing), which you can find at https://laconteconsulting.com/blog. She is based near Houston, Texas.

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