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Going on Offense With Defensive Employees

Some employees are painfully defensive. That makes communicating, learning and growing really uncomfortable.

I can get all judgy and call this a character flaw that manifests from insecurity. I can get all Freud-y and say that insecurity stems from some unknown battle they grew up fighting with their parents or friends.

I can read Radical Candor by Kim Scott, and No Rules Rules by Reed Hastings. Both are incredibly insightful.

Or, I can poll my entrepreneur friends from EO to see how they deal with defensive employees in their companies.  Here’s what some of them said:

  • “I can’t claim to have figured that out. I always try to set the context for difficult conversations. Two other books that have really helped me are Dare to Lead by Brene Brown with the concept of a “Rumble” which has its own rules. And Ed Catmull wrote Creativity Inc. which goes deep on how candor is essential in Pixar’s culture. My personal application of learning here can be summarized by setting the context for getting feedback before giving it and working hard to structure it so it’s not personal and strictly focused on the work challenge at hand.” – Garry Polmateer, CEO at RedArgyle
  • “I just listened to this TED Talk: WorkLife with Adam Grant: How to love criticism. What if you could tell your co-workers what you really think of them? At the world’s most successful hedge fund, everyone is rated and ranked constantly — in front of everyone. They’ve figured out how to embrace negative feedback, and they swear it’s essential to their success. Adam Grant shows how you can learn to take criticism well — and get better at dishing it out.” – Harris Wolin, Partner at Myers Wolin, LLC
  • “In my experience in these situations, leaders will kill themselves to try to get some people to behave better, and in very few cases do they get any kind of result. From what I’ve seen, this outcome occurs for two reasons:
  1. The leader exhibits the same behaviors but refuses to acknowledge them. ‘She’s defensive, but I’m not, I’m just certain and I don’t want to waste time!’
  2. Employers are afraid to truly challenge these types of employees because they fear the backlash, and they want the outstanding results they get in some areas.

If your best salesperson is super abrasive in meetings, are you really willing to say – ‘If you don’t change how you behave in meetings, you’re fired.’ If not, no change will occur. Making personal change is HARD and people don’t do it just because you want them to. People need to be internally driven to make personal change, it starts inside and comes outside in the form of looking for help. The art of leadership is not deciding what you might do, it’s looking at EVERYTHING you can do, and then spending your time on only the MOST valuable thing. Where will your hour get you the GREATEST result? It’s usually not from arguing with the obnoxious person again about their inability to take feedback. It probably is working with the quiet person who is eager for help, but afraid to ‘bother you’ and who will thrive in your organization with some 1-1 boss time.” – Zac Cramer, CEO at IT Assurance

  • The Five Dysfunctions of a Team‘ presents the concept that underlying trust is healthy conflict. I experienced this firsthand from my leadership experience. I am low-key and discovered my “nice guy” personality left team members distrusting me. Mix in some Radical Candor and instead of being negative, it opened trust as everyone knew where they stood. As for the defensive employees, I had to switch to a more questioning vs telling conversation. ‘How do you think you are doing?’ ‘I would like to know more about that…’ Honestly, in our line of work, the defensive employees are probably not going to cut it anyway because it will torpedo a client relationship.”– Paul Fury, CEO at The Fury Group
  • “We have a core value called ‘Mean it without being mean’ that attempts to normalize direct communication and put focus on the practices of Radical Candor. I agree 100% with Zac in terms of modeling. Be the change you wish to see!” – Adam Butler, Founder & CEO at The Butler Bros

My own personal hack – meet with the employee face-to-face, empathize and seek to understand, and then rip off the band-aid as tactfully and professionally as possible.  The pain of waiting usually exceeds the discomfort of the difficult conversation itself.  (I think I’m going to tweak my approach based on the above though. These guys know their stuff…)

-Alex Gertsburg, Esq. 


Our Top Blog Articles This Year

We’re always looking for feedback on what issues are most pressing for your business. If you’d like to see certain topics covered on our blog, The Fix, shoot us a note, and we’ll do our best to highlight your topic in an upcoming edition of the newsletter.

In the meantime, check out our most popular posts this year, and don’t forget to subscribe to get new articles sent directly to your inbox:

  1. Six Benefits of Hiring an M&A Advisor to Sell Your Business – Michael Callam, President of Gertsburg Licata’s Talent and M&A advisory groups
  2. Drafting Customer Contracts that are Enforceable Louis J. Licata, Esq., Managing Partner & Michael Beardsley, Esq., Associate Attorney
  3. What Ohio Business Owners Need to Know about Verbal and Written Employment AgreementsAlex Gertsburg, Esq., Managing Partner
  4. Simple Steps to Keep Liability Limited to Your LLC – Eugene Friedman, Esq., Partner
  5. Can Employers Require Employees to Receive COVID Vaccines?Maximilian Julian, Esq., Partner


Senior Legal Recruiter

The best thing about 2021 (besides launching a brand new firm, establishing our new headquarters, and helping hundreds of clients achieve their business goals!), has been welcoming several new attorneys to the firm. 2022 is also gearing up to be an expansion year and we seek a key player to join the team and make this vision a reality. 

As such, we have a current opening for a dedicated, in-house recruiter to manage our attorney recruitment and onboarding process. 

Extensive recruitment and legal industry experience is required. The position carries above-market compensation and benefits commensurate with experience and verifiable results. See the full position details here and please feel free to share with qualified individuals.

Questions about the position? Email [email protected].


Risk Assessment

Preparing your business for sale is essential to ensure a smooth transaction. Many CEOs are blindsided when a sale slows or is terminated due to diligence issues. 

If you’re seeking to prep your business for market, or if you simply want to ensure your business isn’t exposed to expensive litigation, take a few moments to take our risk assessment survey to see if there are simple steps you can take to protect your business and set yourself up for a successful exit. 

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Mastering the Art of Failing

An entrepreneurial reality check infographic: How Elon Musk Failed Before He Succeeded.

-Alex Gertsburg, Esq.

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