Have the Courage to Be Direct

Tsun-yan Hsieh, a long-time counselor to corporate leaders and one of my co-authors on the book Heart, Smarts, Guts, and Luck, once surveyed a group of global CEOs and senior executives about whether they thought their meetings met the intended objectives. Only about 40% of the meetings did. How can this be? The answer lies at least in part in the human tendency to avoid or massage the delivery of difficult or conflict-causing topics. Unfortunately, these are precisely the moments where directness is most needed.

Being self aware about the types of conversations and meetings that demand increased frankness is a starting point for more efficient and effective communications — and, most importantly, mutual respect. Here are some principles to aid in this quest:

1. Know the why. Are you clear on the reason for the conversation or meeting? Have you made that objective immediately and absolutely clear to your meeting counterpart? I vividly remember the first time this lesson struck me in the face. I was meeting with a senior executive from IBM some years ago when I was running an Internet advisory and services firm. Within the first two minutes, just after the requisite pleasantries, he asked: "What do you hope to accomplish with this meeting, and how much time do we have?" I was at first taken aback as I realized I was not clear on my own objectives. I had thought more about how to run the meeting than the "why" of the meeting. When I thought about it, I realized I had simply wanted to use the time to get to know each other in the hopes of discovering possibilities for collaboration. But I could have made it more concrete by saying, for example, that my end goal was to see if there is a partner deal opportunity between our firms. The executive's simple question created permission for positive assertiveness. Try asking at the beginning of more of your meetings some variant of the question, "What do we hope to accomplish here?" Another helpful tip is to recognize that almost all meetings fit into one of three buckets — gaining input, informing (e.g. "level-setting"), or requesting approval. Always be clear which sort of meeting you're calling.

2. Don't sandwich bad news. When you are delivering feedback (which happens in a meeting or conversation that fits in the "informing" bucket), avoid the too-common practice of mixing good news with bad news. This can often send a mixed message. The classic feedback "sandwich" goes like this: good news, followed by bad news, ending with good news. Eating a sandwich with good bread, but bad meat in the middle, isn't too enjoyable. And while giving someone feedback in a considerate, contextualized, and balanced manner is of course good practice, you need to be very clear and direct on the poor performance part. It is often the most important aspect of a feedback session, and sadly tends to get muddled.

3. Go ahead and ask. My venture-capitalist colleagues and I are accustomed to receiving pitches. But we are surprised by the number of times the ask is not clear or is made as a thinly veiled subterfuge towards a different ask. For example, when an entrepreneur says, "I would love for you to just give feedback on our business plan," but the real ask is "I would love for you to write a check for our business." When you have an ask, it is best for all parties that it be clear and transparent. It is much better just to say: "I would love to see if you might be interested in investing in our concept, but even if you're not, I really want your feedback." The takeaway: when you have an ask, just ask.

When we avoid conflict or try to skirt directness, it does a disservice to all involved, and often just plain wastes time. Consider the potential outcomes if you avoid directness:

• People leave the meeting thinking it was a good session, but they are not actually aligned, or
• People leave a little foggy as to the purpose and next steps.

Both outcomes lead to confusion, and often passive-aggressiveness ensues. And things often only get worse people then seek resolution through email and texts — such communication methods with have a tendency to spiral in the wrong direction.

Being assertive and direct does not need to mean being cold and hard. The tone you use and the words you choose (e.g. in the "investment ask" example above) matter a lot. But you will likely get more respect from being direct than by overthinking the positioning of a message or meeting.

Diplomacy is a great virtue but so is clarity, and diplomacy without our clarity is just undiplomatic