Early in my career, I was hesitant to be direct with people, lest they think I was too aggressive. Whoo boy did that ever get beaten out of me the hard way. And I’m not the only one.

Today I want to talk about one of the most common developmental paths for a scale-up founder: transforming from a “nice guy” to a strong, direct communicator. 

This is a fraught process, but the rewards are immense. Let’s dive in. 

On Directness

Some leaders have developed a comfort with direct communication. Some leaders speak clearly, say what they mean confidently, and don’t waste words. They don’t wrap their communication in fluff to help it go down easier, and they don’t second guess themselves. Some leaders simply communicate directly. 

But most leaders don’t. 

Indirect communication is the default for most people, so when most leaders want to say something important, they don’t get to the point. Instead, they set themselves up with a few preceding points, or they say almost what they mean to say, using many words instead of few, hoping the other person will figure out their intended message. If the other person doesn’t intuit the leader’s intent by magic or effort, indirect communication can often lead to resentment, frustration from both parties, and still more indirect communication, which further obfuscates what’s really going on. In a circus mirror attempt at being “nice,” or at least at being perceived as being nice by not saying anything too harsh, the indirect speaker risks saying many words, communicating nothing, and having both parties less connected with each other, and with reality, for the effort. 

What was the point of that last paragraph? I’m not even sure I know. But it sounded pretty. Such is indirect communication.

Nobody is born knowing how to communicate. We learn how to communicate – the words we say, how we use or are used by silence, how directly we approach what we mean, and even how we pronounce words – when we are children, from those around us, typically our family of origin. 

For a child to learn to communicate directly, they must be born and raised inside an environment that rewards that kind of communication. And despite what we might tell ourselves, it’s a rare set of parents that reward Junior when he says “I want an ice cream, please.” More often, kids are rewarded with treats when they are cute. Or persistent. Or when they pit mom against dad. Or when they cry. Or when they do what their told. Or when they withhold information or love. Or any other of a nearly infinite number of techniques that pull on mom and dad’s heart strings. 

And we wonder where we learn to communicate so obtusely. 

People who naturally communicate directly are typically those who had to grow up early, and accordingly were put in situations in which they had to regularly communicate with grown ups outside the family — i.e. those who were more immune to their cute, childhood charms. 

Indirect communication comes from fear

Indirect communication is not “nice.” It’s ineffective. 

Notice that leaders most often communicate indirectly in difficult situations. In fact, their tendency to communicate indirectly, hedge, use verbal crutches, second guess themselves, and talk way longer than they need to, increases linearly with the degree of difficulty they perceive that the receiver will have receiving the communication. Indirect communication is a way of backing into a necessary communication, hiding one’s eyes and vulnerable parts, and hoping to simply get it over with. 

Indirect communication doesn’t come from a place of generosity or kindheartedness, as most indirect communicators tell themselves. Indirect communication is a symptom of unexamined fear on the part of the speaker (notice that even the most sideways communicator doesn’t speak indirectly when asking about the weather. Or sports scores).

Indirect communication comes from a person not trusting themselves or their ideas. It is a way to prioritize maintaining a connection with another person, however shallow or false, over actually communicating what’s true for them and risking the other person’s disapproval. 

At its core, indirect communication is a symptom of a (usually unexplored) insecurity that one will be rejected.  

Indirect communication destroys psychological safety

A client of mine was surprised to learn from an exit interview conducted with his company’s  Head of People, that an exiting employee of his had been scared of him the entire time she’d worked at the company. He was particularly shocked considering how nice he thought he had been to the employee. How he’d bent over backward to give her the benefit of the doubt and heaps of praise.

“Did she do good work?” I asked.

“I mean, not really. Honestly she wasn’t that great.”

“Did you tell her that?”

“Not in so many words. She was good enough, so I just mostly let it go. I really liked her though, that’s why it’s so crazy that she was scared of me.” 

“I know it seems that way. To confirm, you communicated verbally about how good of a job she was doing, but inside you felt like she wasn’t getting it done?” 

He nodded, grimacing at the disconnection I’d pointed out. 

“I see you making that face right now. In my experience, your facial expressions are quite illustrative,” I continued. “Do you think she might have noticed how you really felt, sometimes?”

He paused. “Yeah, probably.” 

“I wonder how it would feel to have your boss tell you that you’re doing a good job but have that person communicate something different through their facial expressions? Or through their actions?” 

“Probably pretty confusing, I guess,” he said. “Maybe scary.” 

Per HBR, psychological safety is “a shared belief held by members of a team that it’s OK to take risks, to express their ideas and concerns, to speak up with questions, and to admit mistakes — all without fear of negative consequences.”

Core to psychological safety is a belief throughout a team that they know the score. They understand what they’re here to do, what the goal is, and how well they’re doing toward that goal. Direct communication is essential for this. 

On the other hand, if someone is not meeting expectations, but their manager communicates that indirectly, in a way that the communication is unclear as per the example above, it creates confusion inside the person, and the team. What are the standards? Are we doing well? What does our leader actually want? Thus, a team begins to question itself. And with those questions, psychological safety begins to die. 

Psychological safety is a prerequisite for company performance. And direct communication, especially about difficult topics, supports clarity, and clarity is a prerequisite for psychological safety. 

Being overly “nice” (distinct from “kind,” which can be held in tandem with directness) in leadership often has the opposite effect you intend. 

How to learn to communicate more directly

You might be an indirect communicator. And the honest truth is, for most people, that’s probably fine. Unless you’re leading an organization, in which case you are probably already aware of the tremendous cost of communicating indirectly, because your entire organization is likely ripe with passive aggressiveness, unmet expectations, and frustration. After all, the psychology of the leader is the psychology of the organization. 

Leaders looking to train themselves to communicate more directly must progress along two paths: First, they must explore and heal their fear of rejection. Second, they must practice communicating directly.

Starting with the first step, we can explore and work toward healing this fear of rejection by noticing it in the moment, and working to understand and heal the parts of ourselves that are scared. 

Here’s how to get started: 

1. For a week, at the end of each meeting, spend five minutes reviewing your communication. Where did you communicate directly? Where did you communicate indirectly, or otherwise communicate something different than what you really think?

2. At the end of the week, organize all the instances into an inventory of all your indirect communication, identifying patterns around types of information and/or specific people or situations in which you default to indirect communication. Organize the identified patterns in order of frequency. 

3. If you have a coach, work with your coach to unpack and heal those scared parts of yourself. 

4. If you don’t, find a quiet place and 30 minutes. Starting with the most frequent fear, interpret your fear using the somatic sensing model outlined here. More details about the science of how this model works, here.

Over time, you’ll find that as you heal the underlying fears that are driving your indirect communication, you naturally feel more comfortable being direct. 

Next, or in parallel, you must practice. 

Using your inventory, much of practicing amounts to noticing where your pattern is to communicate indirectly, and then when you find yourself in that situation, or communicating with that person, slow down, consciously speak directly, and make sure you say everything that you think. Check, near the tail end of that conversation, to ensure you’re holding nothing back. 

Then, after each relevant meeting, review yourself according to the process above.

It takes time, and it takes reps, but in my experience, with sufficient attention, every CEO can learn to communicate directly. 

A note on the process

In order to scale a company of any size, a leader must learn to stop being manipulatively “nice,” and start communicating directly. 

But for those for whom that’s not natural, this process will make you feel as if people don’t like you.

This is normal.

It feels this way because "nice" people are so used to optimizing for getting along with people that they confuse people pushing back with people not liking them.

This causes people to relapse into niceness because it plays on the very reason they were nice in the first place.

But people pushing back =/= people not liking you.

In leadership you WANT people to push back. Often. It's what makes you both better. 

Most leaders know this intellectually but still are surprised by just how yucky it feels when they first start experimenting with directness, after a lifetime of pleasantries.

If you are on your own journey toward being more direct, just know that it's normal for this part of leadership development to tweak your ego, more so than many others. 

Keep going.

Want to dive deeper?

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Executive Coaching for Entrepreneurs

There’s a reason every elite athlete in the world works with a coach. You need more than one perspective to see your best work.

I’m an executive coach and the founder of Inside-Out Leadership, a boutique leadership development agency that supports entrepreneurs to step fully into their lives, and transform their companies into their masterpieces.

Leveraging 15-years as a founder/CEO, along with deep training in mindfulness, psychology, Neurolinguistic Programming, psychedelic integration and more, I have helped leaders from some of the fastest growing companies and VC funds in the world design a more conscious life and make key changes to improve their performance and satisfaction.

I coach leaders how I want to be coached:

• Focused on the person, not the role.

• Focused on results, without the fluff.

To learn more about working with me, click here.