How to Deal with Difficult Conversations: Elevate It

By Dougal Cameron - April 03, 2020

Difficult conversations are common occurrences for anyone running a business. B2B SaaS firms are no exception to this rule. Knowing how to set the stage for the best outcome is more art than science.

Dougal Cameron with GSV shares with us today his approach to handling tough conversations.

Put yourself in this position for a moment.

The Situation

It is a sunny Friday afternoon in the middle of April. The day is winding down and you are looking forward to an evening with friends on the outdoor patio at a nearby restaurant. Suddenly the ‘ding’ of your email client jolts you back to reality.

The email is from one of your customers. The subject reads “Issues” and the first eight words viewable in your email client read: “There better be a good explanation for thi…”

“Ugh,” you moan, this day might not be done after all.

Upon closer inspection, you see the customer is forwarding you an email from your team member who had let him know the extra requirements added have increased the costs by ten percent. You are a little perturbed because you distinctly recall bringing this cost increase up with him four weeks ago and even have an email clarification with him substantiating the approval. You did everything right.

What do you do next? Go…

Behaviors impact understanding under stress

If you are like most people your instinct is to hit reply and start an email response. If you are slightly nicer than average, you might not directly confront him with the date and time of the email-based approval for the cost increase. You might, in fact, go as far as to explain that he might have forgotten the conversation that you two had in which these cost increases were discussed and approved. If you are like most people, your instinct on this is wrong.

Email creates the worst blend of immediate information stimulus and gives the opportunity for an immediate reaction. This means you can still be processing the tone, content, and impact of a message while simultaneously writing and even sending a response. In addition, our societal addiction with immediacy creates a frantic desire for a quick reply that often overwhelms our desire to edit and refine the message. This mixed with a potentially angry or at the very least unhappy recipient is a perfect recipe for a miscommunication and an escalation of tempers.

Face-to-face and verbal interactions give a much deeper level of insight for communication. Verbal tone, facial tone, and body language all modify the content to inform the recipient of the true meaning. The meaning behind contents of an email are subject to the attitude and perception of the reader at the time.

Michael Morris and Jeff Lowenstein are among the scholars researching email as a communication medium. They identified three major problems with email that have the potential to distort the intended meaning:

  1. Email lacks cues like facial expressions and tone of voice
  2. The prospect of instantaneous communication creates a sense of urgency that can lead to carelessness
  3. The inability to develop personal rapport over email makes relationships fragile in the face of conflict

Due to these limitations, email tends to feed the preconceptions of the recipient while phone conversations remove the distortion of perceptions. This point was illustrated in a study where women were asked at Cornell to interview candidates for hire. Half were to be interviewed by email and half by phone. In reality, the phone interviewees’ responses were transcribed and emailed to the interviewers as the email-interview candidates. Then each interviewer was shown a picture of the candidate; either an Asian or African-American woman when in fact all interviewees were white. Email based responses showed a clear racial bias for the African-American picture group over the Asian picture group which almost completely disappeared in the phone-based responses. Email magnifies miscommunications and mis-perceptions.

Email is also ripe for a condition called cyber disinhibition. This is when with asynchronous communications you don’t have aid of emotional stimuli to moderate your response which means you are more prone to say things you wouldn’t otherwise say to someone’s face.

When you mix the distortion effect of email with the fundamental attribution error (also known as the correspondence effect), you have a truly dangerous concoction. The fundamental attribution error is the observed psychological phenomenon that manifests in people putting undo emphasis on internal characteristics when attributing root cause to a negative stimulus from others while explaining away a similar personal action as justified due to external factors. For example, the correspondence effect would say that a fellow driver would be considered ‘an awful person’ after cutting you off in traffic while you would justify cutting someone else off by the reality of running late to an appointment.

The fundamental attribution error means that the miscommunication or misperception when taken negatively can radically distort a relationship. Friends can quickly become enemies when a text or email is misread and then the source of that negative stimuli attributed to the internal characteristic of the sender. 

The Solution – Level-up the conversation.

The appropriate way to diffuse a tense situation is to level up the conversation. This means a phone call. Or, if the tense encounter was a phone call, then an in-person meeting. Tense situations require good communication and good communication depends upon the intended meaning getting to the recipient. And in tense situations, the recipient often has well-formed and rigid preconceptions.

As a rule of thumb, always lean in to tense encounters. Increase the communication medium to prevent miscommunications and misperceptions from destroying a relationship. You might be surprised by the reception on the other end.


Running toward a tough conversation and leveling up the communication mode is not easy or comfortable. In fact, it is often the most uncomfortable thing to do.

The fear of an explosion is palpable. However, it is far more likely that this fear is preventing effective communication, ironically resulting in a prolonging of the discomfort and an eventual manifestation of the same explosion. Hence, level up the conversation.

If, in the presence of clear unemotional logic the other side is unmoving and irrational, then you know it wasn’t due to behavioral distortions. The other side might be a difficult person, in which case I recommend this book.



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