Having The Tough Conversations – With Lorena Healey

If it’s not uncomfortable, you’re not going hard enough

A few years ago, I was in the office of a senior executive asking for advice on a tough conversation I had been dreading. I was planning to raise a sensitive issue with a peer and was looking forward to it in the same way most people look forward to a root canal!

His advice was simple. He said ‘if it’s not uncomfortable, you are not going hard enough’.

I remember thanking him at the time, and privately rejecting the idea that I had to ‘go hard’ to get my message across. I was a believer that being honest and fair does not necessarily mean tough and ruthless and that I could be direct without reducing the person to a withering mess.

The issue I was addressing was related to the way my peer had run a project meeting, and the off-handed way she had treated the team. I knew she was unaware of the impact of her actions, so my feedback was going to be a shock for her to hear.

So, with all of the confidence of someone settling in for a 2 hour dental procedure, I asked to speak with her. We politely dissected how the meeting had gone, and agreed a plan for how the next meeting was going to run. All of a sudden it hit me. Agreeing a plan that might actually address the problem without really having to address why it was an issue in the first place meant I could hover in the safe territory of generalities and abort the more difficult mission.

The truth here is difficult to admit. I’d like to say that the reason I wanted to avoid the tricky bit of the conversation was to protect my peer’s feelings. The honest truth though, is that was possibly 50% of the reason at best. The other half of the reason was that I didn’t want to feel uncomfortable.

I have since worked with many Managers who recognise this scenario all too well. We know intuitively what we need to say, but sometimes the difficulty in actually saying it means we can soften the blow and pull our punches, just at the time that it’s most dangerous to do so.

And so the ‘going hard enough’ advice took on a different meaning for me. It wasn’t the way I needed to deliver the message that had to be hard, it was the message itself.

Here are 3 tips that I share with Managers, to turn this into action;

  1. Plan your message prior to starting the conversation. This only needs to capture what the 2 or 3 key messages are that you need to deliver. If you are clear on the core messages you need to send, you can check yourself before winding up to ensure you have actually said them. Hold yourself accountable to saying them, even if you have danced around them during the conversation.
  2. Ask yourself this: If the person was to leave this meeting right now, and someone asked them to replay what was said, what message would they have received? Would it be the same as the one you had intended to give? If there is any doubt in your mind, don’t end the conversation until you’ve said ‘let me be clear…..’ and ensure you’ve covered your 2 or 3 key messages. This will eliminate any doubt that you have softened the message, and that they have heard it.
  3. Lead with the most difficult bit first. Those that know they are prone to start a conversation softly, and work their way up to dealing with the issue, run the risk that they either run out of time, or abort when things get tough. Remove this risk by ripping that proverbial band aid right off at the start. Lead with, “I need to talk to you about…..’ and jump right in. You then have the rest of the meeting to explore how they feel about it and what can be done, which is likely to yield far better results. And the added bonus is that the feeling of uncomfortableness tends to dissipate once the hardest part is over.

Tough Conversations Infographic

Delivering hard messages is tough but we should acknowledge that as Leaders it’s always going to be part of the gig. Perhaps we need to get comfortable with the knowledge that we are actually uncomfortable because we are doing the right thing.

Lorena Healey

3Here at Gender Gap Gone we look to Lorena as a Guru of Culture and Change, working at both organisational level and with individual leaders.

But in truth her scope is far broader than that. After a foundation in accounting with PWC, Lorena worked in HR for a global professional services firm before migrating to Seek in 2006- then a domestic employment classifieds business. Through rapid expansion in services and geography, Lorena’s initiatives in organisational development, performance managment and talent strategies contributed to ensuring the business had the culture it needed to execute it’s ambitious business strategies. With Seek nudging the ASX top 50 and recognised as a Hewitt Best Employer – still with the magic of a start-up culture, in 2014 Lorena left to create Lorena Healey Consulting.  

Aligning cultures with business strategies, Lorena is a pragmatic organisational development practitioner, passionate about making business better.

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