17 Types of Challenging Conversations that Defined My Career Success

“You’ll go as far as you are able to communicate.”

Those were the words one of the firm’s vice-presidents shared with me during my first job out of college.

I don’t think I appreciated how incredibly powerful his guidance was until a bit later in my career.

His awkward phrase crept back into my mind regularly during the ensuing decades.

At Least 17 Types of Challenging Conversations that Contributed to My Career Success:

I heard, “You’ll go as far as you are able to communicate,” in all manner of settings.

When I needed to deliver an uncomfortable feedback message.
Every time I pitched a major investment or new strategy.
When I’ve had the privilege of coaching high potentials.
When I’ve had to terminate people for cause.
Recruiting key people to join me.
Negotiating internally for budgets and headcount.
Navigating complex, competitive selling situations.
Leading project teams.
Explaining to a board of directors what went wrong and what I was doing to fix it!
Dealing with clients during a product quality disaster.
Negotiating pricing with suppliers.
Talking with the analysts who bestow the mantle of “market leader” on firms.
Learning to be a real team member of a management group.
Convincing my peers of the need for a strategy shift.
Explaining why we were restructuring to my team.
Working with individuals across many cultures.
Working to get a company on board with strategic change.

“You’ll go as far as you are able to communicate.” Click To TweetI failed in a few of those discussions. In hindsight, I cringe thinking about my awkward navigation of the failures. Tough, good lessons.

But mostly, I succeeded with my challenging conversations because I worked hard to cultivate the communication skills, approaches, and tools essential for success.

Hard Work: The Dirty Little Secret to Developing as an Effective Communicator:

It took deliberate effort to learn to succeed more than fail with challenging conversations.

I observed great communicators in action and attempted to decipher what made them great.

I studied (and still do) everything I can get my hands on regarding interpersonal communication.

I became a student of negotiation practices and approaches.

I learned to lead groups using parallel thinking approaches.

I adapted a public relations technique to develop my approach for message mapping—the single most valuable communication planning tool I’ve found.

And I practiced. Every day. (I still do.)

And, I owe it to that vice-president who has been speaking to me for 30 years, saying, “You’ll go as far as you are able to communicate.”

We All Need to Learn to Succeed with Challenging Conversations:

As I’ve shifted from running businesses to supporting the development of senior and emerging leaders, the importance of developing competence at the challenging conversations is reinforced daily.

100-percent of my coaching calls involve discussing or strategizing with individuals on an upcoming or overdue challenging conversation. The conversations change in scale and scope with title, but the human elements are the same, regardless of level.
Every project or management team performance problem has a communication issue at or near the root cause.
Performance feedback is regularly ignored or if given, mostly massacred.
In my workshop programs, I regularly hear that managers have not been trained for navigating challenging conversations.
Even fewer have been trained on negotiation, which is unfortunate, because this is the single most useful skill in the workplace.
Nearly everyone indicates they would like more performance feedback.
The most popular modules in my online leadership development programs are the communication modules where I share approaches on preparing for and conducting constructive feedback and coaching conversations.
Workshop participants regularly cite: delivering performance feedback and communicating with executives to be their two most difficult communication challenges.

Don’t Leave Performance or Career Success on the Table:

The life of a manager, project manager, team-lead or executive is punctuated by the need to conduct frequent, challenging conversations.

If you’re not having these conversations, you’re leaving performance on the table and doing a disservice to your team and firm.

If you’re not working hard to strengthen your skills for navigating challenging conversations, you’re limiting opportunities for career advancement.

My counsel:

Read widely on this topic. (Nick Morgan, Leigh Thompson, William Ury, Edward De Bono, the Crucial Conversations series.)

Study the great communicators around you.

Practice.

Get trained.

Practice some more.

Learn from your failures.

Keep improving.

(FYI a word from your sponsor: I kick-off a new online, blended training/coaching program: Succeeding with Challenging Conversations, beginning in January. I’m excited to share what I’ve learned about getting this right in 4 live (online) training events plus two open mic q/a online sessions where your questions drive the content. And yes, there’s a personal, one-hour one-on-one coaching session with me. This is the best professional development deal you will find this or any year!)