How to Keep Your Soft Skills From Backfiring

When I started my first business practice I swore to never repeat the same mistakes I had seen my previous bosses make.

I didn’t want anyone working for me to suffer from misogynistic favoritism, inflexibility for time-off requests despite personal tragedy, disorganization, communication breakdowns, lack of transparency, secrecy, envy, sabotage, disregard for psychological safety, and the list goes on.

I would lead the way in soft skills!


I wanted those who worked for me to feel comfortable talking to me about whatever they needed to. I wanted a comfortable, open atmosphere that promoted psychological safety, team cohesion, flexibility for work/life balance , and so forth.

What I didn’t foresee is the underbelly of soft skills:

When you are so focused on promoting psychological safety and communication that you forsake the productivity and efficacy of your employees.


My empathy would get in the way of what I needed certain people to do. I had an employee in a managerial position who confided in me that my personality and position triggered his mother issues.

I would listen and empathize, but week after week he became weak after weak. His work was failing, mistakes abounded, he was spreading a negative atmosphere in the company, but I was afraid to talk to him about it for fear of triggering his past trauma.

There is a point when your soft skills have to work for you and not against you. It’s akin to the motto “know the rules before you break them.”

I definitely believe in leaders cultivating their soft skills but that doesn’t mean they work across the boards in every work environment, in every scenario, and for every employee relationship.

You have to be a bit of a style-flexer and know when to apply soft skills and when to apply good old-fashioned power leadership.

In fact, a recent research study on how a leader’s humility - or lack thereof - affects a team’s creativity, psychological safety, and information sharing.

What the study found is that the effects of a leader’s humility on a team depends on the team’s expectations of a leader.

If the team desires an equal power dynamic within the group then humility in the leadership role has a positive effect on the overall team dynamic: information sharing prevails and psychological safety is cultivated.

If the team, however, desires a leader to take charge and make the important decisions then humility is seen as a weakness and humility can actually hinder psychological safety.

The message is clear:

As a leader, you have to be able to read the room - or the person - and then find the appropriate leadership style.


Here are some soft skill missteps I made and how you can correct them.

Empathy Before Reality


Empathy is an important soft skill for a leader. It shows that you can relate to an individual’s suffering and you won’t indifferently gloss over the events of someone’s life if it doesn’t pertain to the job they were hired to do.

I had a boss early in my career who wouldn’t let me take a day off work to mourn the loss of my cat that I had had since I was in elementary school. That’s when empathy kills employee engagement. (I called in sick anyway)

I discovered that empathy doesn’t always work in your favor though.

Empathy can cause you to keep an employee beyond their expiration date.


Empathy can allow others - knowingly or inadvertently - take advantage of you. Take the aforementioned case of the manager who transferred his mother issues onto me.

I had empathy for his trauma, which in turn led me to speak and behave more gently with him than I normally would have. It led to me not getting the work I needed done because I felt bad about being demanding and didn’t want to be insensitive.

I also employed an office manager well beyond her expiration date because I thought she could learn the ropes if I gave her enough chances. She was young and seemed eager to learn, and I wanted to be someone who gave her the chance to develop professionally and learn the ropes. In the end she quit because her father was sending her on all paid trip to Europe after which she told me she’d be getting “a real job.” Ouch.

The two lessons I learned about empathy in leadership were:

  • Not to keep people beyond their expiration date
  • Don’t let an employee’s emotional issues trump the job you need them to perform

  • Solution? Simple: Cultivate empathy but keep an eye on whether you’re getting what you need as well. Make deadlines. If deadlines come and go without the work completed and you are being asked for an empathy extension, that’s your cue that something’s amiss.

    Flexibility Without Accountability


    I love having people on my teams that thrive in independent work environments. I like to meet and then disband, everyone going off to their respective corners to do what they need to do.

    I don’t have a problem giving time off during the week as long as the work is done. Just because there’s an established 9-6 schedule doesn’t mean you have to adhere to it with military precision.

    I’m flexible, but I do expect things to get done by the established deadline. As a younger and less experienced leader, I fell into the trap of not holding people accountable when deadlines came and went and the work wasn’t done.

    Solution? Have an initial conversation to uncover what kind of work style the person has (particularly in remote working situations) and what they expect from you. Maybe run an assessment on them so you get a glimpse into their personality. I think it’s wise to start from a place of flexibility, but be aware of whether a person’s performance deserves your continued flexibility.

    Related: The Kind of Power That Builds Influence

    “It’s OK, I’ll do it”


    I’m embarrassed to say that at times in my past the above statement felt like a mantra. When an employee expressed work overload or time management issues my autopilot would turn on and say, “It’s OK, I’ll do it.”

    I wasn’t enforcing the same work ethic in others that I was enforcing for myself; I picked up the slack when I was already overloaded with work myself. Then I would find myself disgruntled and resentful, when I was the one who let it happen. Some part of me also believes I can do everything, and this gets me into hot water...with myself!

    Solution? Help prioritize your people’s workflow, when possible. Ask them what’s on their plate and see what can be moved around to allow for everything to get done by the time you need it done. That is actually a soft skill protecting another soft skill!

    By no means am I suggesting throwing out the soft skills - I am a firm believer in soft skills!

    Employee engagement , promoting psychological safety, creating an organizational culture, and supporting your team’s emotional needs are all important aspects of running a successful group of people that will turn your business goals into reality.

    But you also have to keep them in check at times so they don’t run amok. You need to be ready to stand firm and demand the results you require from your people as well. As a leader, you determine when to draw the line in the sand.

    Stay alert to ensure your soft skills don’t hinder your goals. Trial and error will reveal your personal leadership style to you!

    I would love to hear about your own leadership experiences with soft skills!

    KEEP IN TOUCH!