Four habits that will help you stand up for yourself at work

Besides weddings and dentist appointments, the kind of human contact I have dreaded most is a meeting where I need to deliver tough feedback (constructive criticism in HR speak) to another human being.

At work, there is no way to avoid such moments. We work long hours, are always connected and ambiguously defined roles mean our paths cross in unforeseen ways. Today’s workplace is an MRI of the soul, with all our qualities laid bare.

The only way to maintain credibility and influence is to be honest in delivering tough and candid feedback. 

Over my career, I have gone from being a timid people-pleaser to a leader who can confidently deliver my point of view to direct reports and supervisors alike.

Here are four habits that helped me get better, and might help you too:

Do it early and do it often

Human beings often dread tough conversations for several reasons - what if I come off as rude? What if I cave at the last minute? What if I end up destroying the relationship? - the doubts ricochet in our minds and our heartbeat accelerates as the moment draws closer.

I once had a senior colleague who routinely complained about her skip-level boss, the company’s General Counsel. After the first few times, I felt like pointing out that she should probably sort things out with him directly rather than criticizing him behind his back. But I bit my tongue, rationalizing to myself that it was not my place, and that she must trust me so much to be so open with me.

Bad call.

I later discovered that just as she was criticizing her boss in our meetings, she had been criticizing me when talking to others. By not pushing back on her lack of professionalism and transparency sooner, I had enabled her, and become complicit. 

Human relationships are all about expectations - how you conduct yourself early on often sets the tone for how others perceive you. Once these perceptions are set, they could become indelible and immutable.

Lesson: If you want to deliver a tough message, don’t hide behind hesitation. Bad news, unlike wine, does not get better with time. It rots, gets rancid, then devours and ultimately destroys the relationship.

Ask yourself: what is the desired end state?

The worst thing you can do in preparing tough feedback is not think through what you’d like the post-feedback world to look like.

The fact that you are at this juncture makes obvious that something needs to change - in the short term and the long term - for mutual benefit. You need to be able to articulate this desired change in the context of the overall relationship.

This clear-eyed preparation is vital as you approach high-risk moments, and context-sensitive one-on-one conversations tend to be loaded with risk.

For example, instead of saying:

“Stop interrupting me repeatedly in meetings, you (invective of your choice)”

you might say:

“Let’s make sure we let each other finish, to make sure we understand the same facts, and agree on the right way forward. Otherwise, we might inadvertently end up working against each other just as we are talking over each other.”

Explain what the problem is, how it affects your shared interests, and how doing things differently will help everyone. At a minimum, you’ll come off as a problem-solver rather than a whiner.

List examples, as many as possible

Just as fear makes it hard to deliver tough feedback, anger often makes it all too easy.

We often see the other person as the villain and ourselves as the victims. If only they had listened to me, we would not be here, makes for a very satisfying and self-validating narrative. All these thoughts can fill the echo-chamber of your own mind, and make yourself the wronged warrior in a tragic saga.

Before you give in to your self-righteousness, remember: a scorched earth strategy does not create fertile ground for healing and reconciliation.

I recently had to deliver tough feedback to a well-meaning but impatient superior. Rather than blaming them for the end result of a recent project, I listed specific interactions leading up to the anti-climax - rushed meetings that ended with divergent understandings of what was required, insufficient understanding of details and external teams that led to unrealistic expectations, frequent interruptions during meetings that affected our collaboration - as examples of accelerants on our path to perdition.

I made the case that I was not assigning blame, but pointing out systemic dynamics that undercut our talents and good intentions, and would continue to do so unless we improved how we worked together.

Lesson: Preparing these examples will help you revisit those events and replay them; you might see patterns or facts you had missed in the moment and be more prepared to have a productive conversation. These examples will also give you and the recipient of your feedback a common set of events to reference and subtract emotions from the exchange.

Listen to their perspective

After all the buildup that goes into a tough conversation, we are often so eager to get our point of view across that we come off as too passionate, but not compassionate. Out of fear of looking weak, we may end up optimizing for potency at the expense of empathy.

The outcome: we fail at listening. We hold on to facts that affirm us while ignoring those that challenge us.

Listening to views that diverge from yours is not a sign of weakness. It does not necessarily mean you are conceding the point.

Listening is a sign of strength in your own maturity and professionalism.

It is also a sign of respect; that you are in this conversation not just for yourself.

The most important benefit of listening to the other perspective while delivering tough feedback is that regardless of where the facts lie, people are more willing to listen to you if they feel like they were listened to.

All great failures - the collapse of Lehman Brothers, Katrina, the botched rollout of Obamacare, the Iraq War with dubious claims of WMD - can be traced back to someone having the right information, but unwilling to call it what it was for fear of making waves and drowning under them, when in fact telling the truth would have helped them sail freely.

That it is right does not make it easy. I get it.

When I was growing up, I was always the good kid in a joint family. Keep rowing on placid waters, and don’t rock the boat was our family ethos. As a result, I was spit into the anarchic world of adulthood ill equipped to stand up for myself.

My early attempts at delivering constructive feedback were clumsy. At times, I came off as Mr. Rogers on decaf - too benign to send the message. At other times, I was over-emotional and it felt like the shower scene from Psycho. Neither approach worked very well.

But I kept trying, and kept improving, and am improving with every such conversation regardless of whether I am receiving critical feedback or dispensing it.

You can do so too.