“What’s one effective way you’ve found to engage in constructive dialogue with those who hold ‘woke’ views? How did this approach work for you, and what advice would you give others?”
Here is what 21 thought leaders had to say.
Listen First, Debate Later: Changing Conversation Dynamics
I engage with those who hold woke views by totally stepping out of the debate mindset. I am not interested at all in scoring points. I remain centered on the thought that when the objective is to comprehend how a particular individual thinks, then I must cease trying to win. As soon as I began to listen without an intention of proving wrong, the whole dynamics changed. Discussions that normally stall started to flow.
There is a discussion that I had with a student at the university who was highly pushing the idea of decolonization of all the business systems. My instinct was to challenge it but I restrained myself and replied, “Take me through what you may mean by that in the context of managing a storage facility with 200,000 square feet of storage at several rural and suburban locations.” I meant it literally. That response lowered the temperature of the exchange. We ended up talking through hiring practices, pricing structures and vendor selection.
Faraz Hemani, Chief Executive Officer, Iron Storage
Find Common Ground to Transform Debate into Exchange
If I am speaking with someone who has strong progressive or ideological views, I will find one area where I truly agree, even if it is only a minor thing. Then I use that shared ground to generate conversation without attempting to drive a point. When they bring up issues that really do make sense or point out areas I might have missed, I tell them so right away. That changes the dynamic of debate to exchange and it removes the pressure out of the dialogue. When you are being fair people can tell and this is why they are open.
I remember very well during one client meeting where the discussion veered into environmental shipping policies. I did not agree with the blanket statements being applied to the logistics companies, but I did not immediately reject them. I agreed that more transparency is needed on emissions data and shared what we were doing around route optimisation to reduce fuel use. That led to a more even-handed discussion and we ended up talking about feasible solutions not ideological stands. I managed to save the reputation of our company and build rapport without losing my position. It is not weak to give when it is logical, it is a tactic. It makes you seem like you are listening and not merely waiting to argue.
Allan Hou, Sales Director, TSL Australia
Respect Trumps Ego in Ideological Discussions
Whenever I end up in a conversation with someone who has strong progressive views, I make sure that sarcasm never enters the picture. The moment you start mocking someone’s perspective, even slightly, you shut the door on anything useful. I have seen this happen in agency settings, especially in creative review meetings where someone tries to be clever at another person’s expense. It kills any momentum and pulls the whole tone all the way down into the defensive and pettiness.
I have had better outcomes by treating the other person’s view with the same care I would expect if the roles were reversed. In a recent project review, one of which featured a campaign that was heavy on gender identity messaging, the more traditional stakeholders were tempted to roll their eyes. I nipped that in the bud and told everyone to back off on the commentary and just concentrate on the results we were after. As soon as the room realized that no one was in the room to score points, the energy changed. It enabled us to talk about effectiveness, rather than ideology. Respect proved to be more effective than ego. It was able to save us a minimum of 8,000 dollars in possible reshoots and compress our campaign delivery window to 3 days.
Sean Clancy, Digital Marketer & Managing Director, SEO Gold Coast
Summarize My View, I’ll Summarize Yours
Whenever I encounter somebody with ideas that are completely different from mine, I will ask them right away to summarize my stance in their own words so I can react to theirs. I point out very clearly that I will do the same to them. This practice compels each of us to be more patient and listen rather than jump into refutations. It forces each of us to avoid assumptions and operate on the actual ideas on the table. I have discovered that when they are trying to explain my stand, they tend to stop on some points that they had not understood well.
In one of the conversations, one person boiled down my premise regarding business meritocracy in a way that completely ignored the skill-development piece of it. As soon as I stated that this was the focus of my point of view, they changed their restatement. I then restated their stand on systemic barriers being careful to give their examples in detail. This process of back and forth lasted approximately twenty minutes, however, it eliminated the majority of misunderstandings that were leading to tension.
Chris Kirksey, CEO / SEO Specialist, Direction.com
Start With Shared Concerns to Maintain Dialogue
Whenever I speak with someone who has strong progressive views, I will right away point to something we both agree on. Even if we look at the issue from different angles, there is usually a shared concern. It may be fairness, safety or the impact of the decisions on others. I do not omit the points that we do not agree on, but I start with that common thread. It maintains the tone even and easier to continue without turning the conversation into an argument.
This worked during a discussion about hiring standards. I said, “I believe that everybody deserves a level playing field and nobody should be denied an opportunity due to factors beyond his/her control.” That brought an opportunity for a true dialogue, where we could explore the subject more without making it personal. When the people realize that I am not arguing a point, they talk straight and less strained. I continue to apply the approach because it leads to actual conversation, even when the topic is tough.
Matt Woodley, Founder & Editor-in-Chief, InternationalMoneyTransfer.com
Neutral Tone Opens Doors to Productive Conversation
I never mock, mimic or let my tone carry any edge of sarcasm, even if I am frustrated or disagree strongly. When that is detected in your body language or tone, the entire conversation closes down. They cease talking, and begin fighting. It turns into a matter of keeping face rather than sharing ideas and that is where the progress dies.
I was talking once with a colleague at my workplace after a diversity seminar. He gave a blanket statement of systemic privilege. I did not agree with his extremes but I maintained a neutral expression and even tone. I put a few questions, and listened. He then softened and we actually got somewhere. He admitted he was speaking out of frustration. I could express my position without either of us having to raise our voices or secluding ourselves in corners. This would not have occurred had I rolled my eyes or cut him off in the middle of his sentence.
Steve Case, Financial & Insurance Consultant, Insurance Hero
Drop Labels, Ask Questions, Shift the Tone
What I do every time I enter a conversation with someone who holds strongly progressive views is drop the labels completely. I don’t use the word “woke” because it shuts the door before the conversation even starts. The label conveys various meanings to different individuals, and it evokes defensiveness in the majority of situations.
I concentrate instead on what the individual is saying. I hear what they are saying about the values, not what someone may call it. If someone’s talking about inclusivity or equity, I ask where that belief came from. Was it something that is personal? Was it a policy they had read about somewhere? Once I shift the tone from “Are you one of those people?” to “Tell me how you got there,” the conversation usually shifts from tense to engaged.
Cal Singh, Head Of Marketing & Partnerships, Equipment Finance Canada
Keep Conversations Calm to Preserve Understanding
I make sure that when I speak with someone who holds strong ideological views, I never allow sarcasm or ridicule to enter the conversation. If I reject their intentions with a joke or a sarcastic remark, the conversation normally goes to a dead end and the possibility of understanding goes out the window. So I maintain the conversation calm and civilized, although I may disagree with most of what they are speaking. That implies allowing them to express their arguments to the fullest and speak calmly to them, demonstrating that I am listening and do not judge every word.
Shaun Bettman, CEO / Chief Mortgage Broker, Eden Emerald Mortgages
Ask How, Not Why, for Better Discussions
When I am having a discussion with a person whose beliefs are quite opposite to mine, I ensure that I direct my questions in a way that makes me seem curious. I will request that they explain to me how they came to their conclusion, and I do not hasten them to my point of view. Such a question enables deeper responses, as it moves the discussion away from defending a position to explaining how that position was formed. It prevents the tone of the conversation from being hostile and allows me to learn more about the values or life experiences that influenced their ideas.
Brad Jackson, Director of Operations | eCommerce Founder, After Action Cigars
Share Perspectives, Not Absolutes, for Open Dialogue
When I am talking to a person who has strong woke beliefs, I refuse to use the first person pronouns in my speech. I indicate the source of my ideas by saying things such as here is how I see this as or on the basis of my experience. That takes the need to agree or disagree off the table and moves the dynamic to a more open one. IIt shows that I am sharing, not instructing. Such a shift of tone serves to keep the discussion down to earth and reciprocal.
As soon as I stop talking in absolutes and begin to put things in my own terms, I begin talking less about getting a point across and more about getting into it. I am not diluting anything but I am stating that I am not trying to ambush or preach to them. That makes things constructive and does not make one defensive. It starts there and I am then able to talk sense without the discussion drifting into labels or assumptions.
Hugh Dixon, Marketing Manager, PSS International Removals
Concrete Examples Beat Abstract Ideological Arguments
By beginning with particular examples that influence daily decision making as opposed to arguing about abstract ideological propositions, I have had constructive conversations with people who are very progressive or socially conscious. In my business, that may translate to discussing hiring policies, material suppliers or marketing slogans. I keep the discussion grounded on a tangible scenario, like using roofing material suppliers who can meet some labor standard, and then break out the trade-offs in price, quality and supply chain stability. This helps to keep the exchange rooted in something quantifiable, at which point the input of insights of both sides can be made without the exchange veering off into abstract reasoning.
When I do this I promise myself to listen more than I talk and even when the talk extends beyond an hour. I will ask them to present me a step by step procedure of how they would solve that very situation including schedules and budget and effects. Once we both go through the math and logistics we can get less concerned with who is right and what works in practice. My recommendation to other people is to pick a common point of reference, which you will be able to measure and analyze each other. It develops a common ground of knowledge on which dispute becomes much more constructive.
Todd Stephenson, Co-founder, Roof Quotes
Understand First, Counter Later with Real Examples
I have witnessed the most productive discussions when I make the effort of understanding where a person has come to develop their point of view before presenting any counter arguments. As a worker in Proximity Plumbing, I have encountered clients and workmates who had their personal opinions about social and cultural matters, and such a conversation will be stressful when it turns into a debate too soon. I make the questions open and give them a chance to express themselves without interference even when it takes me twenty minutes to speak anything of value in response. The tone of that time investment is typically shifted to be open instead of defensive.
When I do answer, I base my arguments on concrete examples of my own life or business dealings and not theory. In case I am going to discuss such a topic as workplace inclusivity, I could tell how we introduced some changes to our hiring process last year and it added three more female plumbers to our staff, increasing our ability to provide services by 15 percent. This turns the discussion into a tangible one and eliminates the abstract politics that tends to drive individuals apart. I recommend: slow down, ask first about the personal context and provide responses based on tangible actions or consequences. It changes the debate of ideological categories into common human experiences.
Emily Demirdonder, Director of Operations & Marketing, Proximity Plumbing
Data Cuts Through Ideology Better Than Debate
Managing marketing across diverse markets like Chicago, San Diego, and Vancouver taught me that data cuts through ideological differences faster than debate. When our team had heated discussions about inclusive marketing campaigns, I pulled UTM tracking data showing our most “progressive” ads actually drove 25% higher conversion rates in traditionally conservative markets.
The breakthrough came during our video tour project rollout. Instead of arguing about representation in our marketing materials, I focused everyone on the shared goal: reducing unit exposure by 50%. When team members saw how diverse casting actually improved our lease-up speed by 25%, the ideological tension dissolved into business strategy discussions.
My approach now is leading with concrete metrics before any philosophical discussion. When negotiating vendor contracts, I’ve noticed that showing ROI data from past “socially conscious” campaigns–like our maintenance FAQ videos that reduced move-in complaints by 30%–gets everyone aligned on outcomes rather than stuck on political labels.
The key is reframing conversations around measurable business impact. Whether someone calls it “woke” or “inclusive,” what matters is that our digital advertising campaigns with diverse targeting increased engagement by 10% and lifted conversions by 9% across our entire portfolio.
Gunnar Blakeway-Walen, Marketing Manager, The Miller Apartments By Flats
Focus on Experiences, Not Labels or Theory
My personal experience has led me to discover that the best kinds of conversations can be started by me merely entering into the conversation with the intent of getting a clear picture of the total experiences that the other person has had instead of merely engaging in a language or labels argument. I enquire about the experiences or incidence that led to their thinking and I narrate on my side of the story in the same proportion and relate it to certain incidences in my work and community life. This takes the conversation out of theory and into real life and this makes it simple to look where we can meet in our priorities.
During one of the talks with a guest, who had firm ideas on the subject of representation in travel marketing, we were talking about a recent renovation I had performed in Ambleside. They challenged the design decisions on a social basis and rather than ignoring their objections, I asked them to accompany me around the property. We talked about the co-existence of design, sustainability and cultural heritage. The communication was also respectful since we based it on something realistic there in front of us.
I would recommend to make the discussion based on a common experience or a specific example. Once the discussion is based on details, it is more difficult to narrow it down to the stereotypes and easier to see the areas where both sides could make a valid contribution.
Marta Pawlik, Creative Director, Interior Designer, Co-Founder & Director, Laik
Shared Goals Transform Opponents into Collaborators
The best strategy that I have discovered is to base the discussion on a definite and practical objective. This approach will change the conversation to one not about broad philosophical concepts but rather a collaboration that has a quantifiable result. As an example, one of my companies was on a project with a large subcontractor whose younger workforce was very concerned about environmental sustainability, a perspective that was new to some of my more experienced electricians. At first the conversation was awkward. Rather than argue about the right or wrong of environmental policy, I suggested to our joint teams that we should challenge ourselves over the next three months to cut our overall project wastage by half.
Such shared, tangible goal changed the situation altogether. The discussion was no longer a discussion of abstract values, but of the means of actually attaining a waste reduction. We began discussing how to recycle the electrical wire insulation coverings, how to dispose of old electrical insulation and how to purchase materials with minimal packaging. The junior staff had certain concepts of what they wanted to do with our waste and my team had been veteran workers and knew what it was like to try and make these alterations on an active work site. It was a collaborative process that saw the participation of six people, and as a result, we were able to measure the decrease in our waste and an enhanced working relationship. We found out that we no longer perceived the other as an opposition in a debate but as individuals who shared a goal. I would suggest others to have a shared goal or some practical issue to be solved. By doing this you can create a bridge of mutual effort and esteem that will hold up a difference of opinion.
Benjamin Tom, Editor | Utility Specialist, Electricity Monster
Ask Open Questions, Then Listen Without Judgment
I find myself around individuals with different points of views most of the time, and I have realized that dealing with individuals who have a woke attitude needs tact and care. The best solution I have been able to find to communicate effectively is to pose open-ended questions and listen to the response.
Rather than giving direct counterarguments, I attempt to inquire into the background of how someone has arrived at this point of view, asking, “What experiences do you have on this issue?” or “How do you think this problem will impact others?” This strategy will help me to get a feel of where the other party is coming to and have an open and respectful dialogue. Individuals that feel listened to will tend to respond and will reciprocate with respect and thoughtfulness.
It has also been of benefit to me to give my own experience of some life or work, which presents the matter in another light, but in a form that encourages discussion instead of closing it. This leaves room to allow both parties to communicate, educate and perhaps even change their opinions in a positive manner.
I would advise other people to speak to such talks with understanding. Do not assume you know what drives people, just be listening to their ideas and react to them in a worthwhile and respectful way. This has enabled me to build more effective discussions even though we are not in agreement.
Michael Benoit, Founder, California Contractor Bond & Insurance Services
Shift from Ideology to Practical Solutions
The most effective way of maintaining any conversation positive is by separating the idea and the presenter of the idea. When one expresses an opinion that could be termed as being woke, I concentrate on learning the result that one wants to get rather than the labeling of this opinion. I have learned that moving the conversation into common ground, a goal like fairness or equal opportunity, will help to lighten the emotional burden of the disagreement. This transition is one that promotes substantial dialogue over the tension.
We were once conducting a public discussion on policies in the work place. One of the participants expressed anger over representation and demanded widespread changes. Rather than debating the premise, I changed the discussion to practicalities, what quantifiable effects would ease their worries and citing examples of gradual policies that had proved successful in other places. The change of ideology to practical solutions transformed a confrontational discussion into a discussion with both parties bringing in ideas. I recommend basing the discussion on specific results and figures, such as percentages or some standards that can be measured, that helps to keep the discussion fruitful and close to reality.
Ryan McCallister, President & Founder, F5 Mortgage
Listen Fully Before Offering Your Perspective
Listening without interruption at the start of the conversation has been the most effective way to keep discussions with people holding strongly “woke” views constructive. When they feel their perspective has been fully heard, they are more open to considering another point of view. I make a point to restate their main argument back to them in my own words, which confirms I understood their position before offering my own. This lowers defensiveness and creates room for a calmer exchange rather than an immediate clash.
Using shared values as the bridge works well. For example, I have had conversations where we disagreed on policy but agreed on the importance of community safety and opportunity. Framing my points around those shared priorities kept the discussion grounded in mutual respect. My advice is to focus on understanding before persuading, because people are more willing to genuinely hear your side when they feel you have taken the time to understand theirs.
Ydette Florendo, Marketing coordinator, A-S Medical Solutions
Listen First, Ask Questions, Find Common Ground
My best experience in dealing with people with whom I disagree is listening to them and not jumping in with my ideas in order to counter theirs.
An especially interesting case is the time that I talked to a colleague about inclusion and representation in gaming culture. I did not argue with them but I just requested them to elaborate the reasons as to why they felt that way. This made me learn their side of the story without making me defensive. Listening and using open questions allowed us to engage in a constructive conversation and have a more effective mutual understanding.
My advice to someone who wants to start having such conversations would be to be open-minded to the conversation and not use dismissive phrases, but ask questions that will help them understand their perspective better. It will be able to change the direction of the discussion and it would become easier to find common ground.
Hone John Tito, Co-founder, Game Host Bros
Stay Calm, Know When to Pause Discussions
It is important to remain calm & polite when talking to Woke people as emotions could build up fast when having sensitive discussions. It is wise to take a break in case you sense tensions rising to stop the situation from getting out of hand. In my experience, I have learned to listen more than I speak. This helps me see their perspective and refine my own views.
The lesson I would advise others is to know when to stop the conversation and when things get heated or unproductive, it is alright to take a step back. Ending the discussion respectfully can leave both sides with room to think and reflect which is far more effective than a heated argument.
Kyle Sobko, CEO, SonderCare
Build Trust Before Tackling Difficult Topics
One of my favorite strategies for engaging with people who are “woke” is the ability to listen and build common ground before diving into a discussion about anything. With Angel City Limo, if a trigger word or subject comes up, I try to remain open and hear it all instead of immediately switching into debate mode. This helps to develop trust with and respect for the group, creating space for a freer, more balanced conversation.
It mitigates defensiveness, allows for open conversation, and goes a long way in showing each person that they have been heard. However, the role of our processes is to convert impending conflicts into collaboration and cross-over learning that reinforces the fabric of our culture and teamwork.
However, my advice to others is to be curious and empathetic. The best way to encourage someone is to ask open-ended questions, avoid assuming or judging, and refrain from trying to “win” the conversation. True engagement creates appreciation and common understanding, enabling good, productive conversations even on difficult topics.
Arsen Misakyan, CEO and Founder, Angel City Limo
