No matter how well you frame your ideas upfront, there will be times when you’ll need to address skepticism and defend your work. These are moments when you can shine. Here's how.
Hi Wes. Amazing piece and the way you string words together reads deliciously. I want to proudly share a moment where I defended my decision using facts, albeit sounding a little defensive (haha). The Filipino culture makes it challenging to defend one’s self because presenting a stance which disagrees with higher ups is often misconstrued as disrespect. It’s difficult to remain calm specially if you feel you’re already at a disadvantage by being younger/lower down the ladder + having the minority view. It’s also difficult to have a discussion when instead of evidence-based logic, you get shot down by “eminence-based” rebuttals AKA “I’m more senior therefore I’m always right.” It’s hard to put forth a valid point if it’s shot down by a slippery slope argument. TL;DR, I would love to practice your advice, but it’s hard to do so due to cultural differences.
I totally hear you Erin. I used to be extremely conflict averse for this reason and had trouble “speaking against” higher ups. I may do a post on how I overcame this. It took years of rewiring. It still doesn’t come as naturally for me as it does for some people. For example, I hear some things that my white sister-in-law jokes about and says to my mother-in-law, and I’m like oh wow, I can’t imagine saying that or seeing any other Asian American saying that to an elder. Of course this played out when interacting with managers in the workplace too. There’s hope though: i actually think I’m quite direct now and as a founder, my job was pretty much to confront. Confront problems, confront ideas, confront people, etc. I have a post I’ve been working on that as well. Anyway, I would love to hear what you said to share and defend your thinking, and what happened. Would you be up for sharing?
I agree with Erin's perspective. As someone raised in Chinese culture, I find that my upbringing significantly influences how I handle such situations. Being confrontational doesn't come naturally to me, and frequently encountering these circumstances is emotionally draining. Moreover, these situations often make me feel nervous and uncomfortable. The cultural aspect adds an extra layer of complexity to navigating these interactions.
Working in a more Western company environment requires a more direct communication style and a willingness to openly demonstrate one's abilities. I'm constantly adjusting and seeking ways to improve so I can perform better in this context. While I've made progress over time - to the point where I'd be more vocal even in a fully Chinese environment now - I sometimes feel as though I'm not being true to myself. This ongoing adaptation process, while necessary for professional growth, can be challenging as it requires balancing cultural values with workplace expectations.
Wes, I’ve always enjoyed reading your articles. Super helpful to me. Thank you!
There's an existing policy which is vague, ambiguous, and outdated. Because of the above features, rules are subject to different interpretations. The more senior members have a conservative interpretation, while the more junior ones have a more liberal take (rule: MDs should not endorse health products; I was defending unpaid skincare/cosmetic reviews are not unethical if done well, but it was shot down). As derms, we are one of the best suited to provide context and free skincare tips. They partially agreed, but insisted ALL branded content - paid or unpaid - is unethical. I explained there were so many angles to sponsored content but they wouldn't accept it so that's that 🤷🏽♀️
Hey Erin, I DMed you but will park this here too. Thanks for sharing more details on the example situation you had in mind. It can be hard to tell if there was room to improve your execution, or if there was no chance your audience would have budged regardless. It’s so situational depending on the logic and narrative of the argument itself. I’ve had clients say they made a strong case, and when they told me, I pointed out areas to improve and they agreed upon seeing it with fresh eyes. Anyway I’m happy to be a gut check to see if there’s anything I’d frame differently if you would find that helpful. If so, feel free to share what you said and how you made the case.
This means a lot, thank you Wamide. What happened earlier this week and how did you respond? If you’d do anything differently, how would you respond now after you’ve read this?
Wow this is such a new concept to me. I viewed defense in any context in a negative light but these tips have changed my perspective. It is possible to defend in an effective and productive way that educates the person who’s asking. Great piece, Wes!
Love this article and I did came across with this many times in my career. Great to know I've done it the right way and thank you for sharing some tips.
When folks challenge your thinking, be sure to accept the challenge and take your oint if view to the next level. Always have a prepared speech or document available to support your views. Never just say stuff to impress folks, coz what you say may be challenged, or even worse implemented without inspection.
Disasters happen fast and easily. So always be prepared for negative comments and have a positive response ready. Know your work and be prepared to do a little extra to convince others if your worth to the team.
A great read and learning, Wes! Being a new manager and trying to change multiple cultural aspects of our org, I do come out strong and need to work on my skills. I acknowledge the gap here.
I’m going to be reading this post multiple times over to truly understand and implement this as a default approach rather than occasional.
However, one other scenario, which I hope you cover eventually, is when the other person is being defensive and how do we resolve those situations. Not sure if you’ve already shared one before (I’m a recent subscriber).
Always great reading your posts and I do make sure to share a few with my wider org on Slack.
There's an extreme to be avoided here, though, which is turning every dang exchange into a Lincoln-Douglas level debate. Sometimes 'thanks for the feedback, we'll consider it' actually is the better response, and sometimes 'ok boss, will do' is the best response. Not always by any means -- context is key.
Agreed. You don’t need to play defense every day, with everyone. A quick answer might be right the majority of the time and there is a risk of going overboard/overcompensating. Like most things, it’s rooted in exercising judgment about your unique situation, reading the person/setting, etc. On a related note, you might like this post on “question behind the question” with examples of when you might want to give a short vs more thorough answer. https://newsletter.weskao.com/p/question-behind-the-question
Think of it as them opening up to your idea...and take advantage of it.
I can relate to this Wes. After 20+ years as a leader, executive, consultant & coach, getting questions is just par for the course, and not always positive ones.
I reframe this as being asked to convince them.
Otherwise they wouldn't ask.
So many gold nuggets in the post but I really liked: "if you explain yourself well, you actually build MORE trust"
Sometimes a Q&A exchange is much better to explain things well, certainly in more detail. And trust building is a wonderful bonus.
Finally, it doesn't have to be confrontational, regardless of how the question was asked.
When they see you not taking offense, you disarm them 😉
Hi Wes, thank you for writing this article. I loved the lesson here and find it valuable. I agree with you on showing and not telling.
Contrastingly, upper leadership has made comments on my rationale like, "Get to the point. This is too tactical. My time is valuable," when I explain an important decision with my work.
“Get to the point” is one of the most common things senior leaders want folks to do. The challenge is it’s extremely situational what is considered too much context/too tactical vs the right amount. Could you share an example? 1) What was the context/purpose/nature of the meeting where you were presenting and talking about your work? 2) How much did your audience of upper leadership know about this topic? 3) What did they ask you and why do you think they asked that? 4) What was your response? With this context, I can better understand where you might have shared too much detail or the wrong kind of detail, and potential takeaways to keep in mind in the future.
This was so timely. I normally like to provide long-form answers when my performance is being questioned, however, I learned from others that this gives the appearance of ego and eliticism. You have restored my initial belief and helped me to once again follow my gut. Thanks, Wes!
Glad you brought this up, HS. A long-form might be appropriate, though I wouldn’t say it’s the default. It also depends on what you consider long-form. In general, I would avoid monologuing for more than a couple minutes before getting some initial feedback on whether you interpreted the question correctly. The biggest risk with diving into a long answer is it can come across as defensive. Check out my post on insecure vibes. Basically you don’t want to seem like you’re overcompensating. If you answer directly (“yes,” “no,” or one line), then share more, this can helps keep your answer focused too. https://newsletter.weskao.com/p/insecure-vibes-are-a-self-fulfilling
FWIW I also tend to answer in more long-form. I think it’s a personality thing. Some people default to answering with short replies even when they should volunteer more context. And others are the opposite. If I’m writing a reply, I like putting my main point at the top, then splitting out the context below. This gives my reader agency so they can keep reading or if they get it/agree early on, they can stop reading. But I generally like volunteering more context because I believe these are opportunities to share and reinforce my team’s strategy, what we are focused on, etc, which builds trust.
I find it very hard to not cross the line between defending and being defensive.
I found that sometimes, your best move is not offense/defense - it’s to take a timeout from the game.
In the examples you shared, the resistance was ‘soft’, and didn’t really endanger the protagonist’s idea/point of view. When some one in authority really questions your idea, and tries to push for a different course, it’s much harder to not get emotional and defensive.
The tips here are golden, and they cover just a single exchange, not the back-and-forth that usually follows. I think it’s for a good reason - after defending my idea, I found it works best to just let it sink in. Often the other side won’t be willing to let it go just because of ego, but when they cool down, they will.
I had multiple cases where senior leaders pushed against an idea, I made my defense and we took a break, and then they came back a few days believing it’s their idea… which is a huge win once you learn to let the “it was mine!” go 😂
I’d love to cover a situation where there’s back and forth that questions an existential premise, Anton. I’ve encountered this many times as I’m sure most folks have. Most discussions/debates on big decisions happen over multiple conversations, sometimes over months. It’s hard to think of a specific example now that those moments have passed though. Also I can think of some potential examples from my work, but they require a lot of context that’s specific to my startup, an issue over time, new information layered in at various phases that changed the situation, stakeholders involved, the anxieties of those stakeholders that changed over time as we got new information from the market, the evolution of my own thinking due to further thinking and/or discussion, etc for a post to be easy to follow for readers. Do you have an example that comes to mind? I’m hoping you do and are willing to share! 🤞
I have a current example one in mind. It's not perfect, but it can work with not too much context:)
Some background:
I'm a director of engineering, leading 2 small engineering teams.
We work with a single product manager, who report to the VP Product.
Our business is in the AgTech industury, which is seasonal.
Our application is heavily used in May-July (the peak of the agricultural season),
and then for 9 months we develop the next version.
Until now, we work with a 'feature roadmap'. The product and executive team
decide what we should work on, and then we develop it, usually spending 1-3 months
per feature, without any validation.
Recently, with the AI hype, we were stopped in the middle of working on a feature I believe in, to work for a new 'AI assistant feature'. Because of the seasonal nature of the business, we were told we have only until the of July to finish the project. We designed the solution, and it's a 2-months project.
Together with the PM, we offered a quick (2-weeks) product that will provide all the capabilities by will require manual work (imagine someone manually prompting ChatGPT in advance). Initially it was shot down, but after I let it go for a while (hence the advice in my comment) the plan was accepted.
And here comes my main problem. I wanted us to use the 2-week version to validate
our customers actually WANT that feature, and then decide whether should we work
to complete the other 6 weeks.
I was told we would do it no matter what, as we always did. There is a solid explanation
(we believe in that feature, if it won't be adopted well we will iterate on the way to adopt it, we need this feature for a funding round), but the problem is it's the same for all the features.
The VP Product & CEO generally agree we should have a validation phase once
I have conversations with them about it, but in reality, the just dictate which
Thank you for taking the time to share this Anton. I’d want to percolate on this a bit more to see where this example would fit and for what topic. It’s probably not possible to remember the back and forth debate around what to do before you and the team landed on an answer. My initial main takeaway from this is sometimes senior management does what they want to do. I have experienced this many times too. But then what’s the lesson? I’d need to think about it more. Regardless I very much appreciate you for sharing here and in the past! Your comment in my finesse essay about how you said “all the data from the past 2 months is wrong” was so perfect. I was just telling folks about your story even yesterday.
Thank you Wes. Yeah, I can understand why the example is not a great fit here. My main lesson from it was that sometimes to get your idea to hold, you need to let go. When ego gets involved, no matter how good your offense/defense, it won't get through.
And I'm glad the other comment proved helpful! I think about that finesse article quite a lot :)
Hi Wes. Amazing piece and the way you string words together reads deliciously. I want to proudly share a moment where I defended my decision using facts, albeit sounding a little defensive (haha). The Filipino culture makes it challenging to defend one’s self because presenting a stance which disagrees with higher ups is often misconstrued as disrespect. It’s difficult to remain calm specially if you feel you’re already at a disadvantage by being younger/lower down the ladder + having the minority view. It’s also difficult to have a discussion when instead of evidence-based logic, you get shot down by “eminence-based” rebuttals AKA “I’m more senior therefore I’m always right.” It’s hard to put forth a valid point if it’s shot down by a slippery slope argument. TL;DR, I would love to practice your advice, but it’s hard to do so due to cultural differences.
I totally hear you Erin. I used to be extremely conflict averse for this reason and had trouble “speaking against” higher ups. I may do a post on how I overcame this. It took years of rewiring. It still doesn’t come as naturally for me as it does for some people. For example, I hear some things that my white sister-in-law jokes about and says to my mother-in-law, and I’m like oh wow, I can’t imagine saying that or seeing any other Asian American saying that to an elder. Of course this played out when interacting with managers in the workplace too. There’s hope though: i actually think I’m quite direct now and as a founder, my job was pretty much to confront. Confront problems, confront ideas, confront people, etc. I have a post I’ve been working on that as well. Anyway, I would love to hear what you said to share and defend your thinking, and what happened. Would you be up for sharing?
I agree with Erin's perspective. As someone raised in Chinese culture, I find that my upbringing significantly influences how I handle such situations. Being confrontational doesn't come naturally to me, and frequently encountering these circumstances is emotionally draining. Moreover, these situations often make me feel nervous and uncomfortable. The cultural aspect adds an extra layer of complexity to navigating these interactions.
Working in a more Western company environment requires a more direct communication style and a willingness to openly demonstrate one's abilities. I'm constantly adjusting and seeking ways to improve so I can perform better in this context. While I've made progress over time - to the point where I'd be more vocal even in a fully Chinese environment now - I sometimes feel as though I'm not being true to myself. This ongoing adaptation process, while necessary for professional growth, can be challenging as it requires balancing cultural values with workplace expectations.
Wes, I’ve always enjoyed reading your articles. Super helpful to me. Thank you!
There's an existing policy which is vague, ambiguous, and outdated. Because of the above features, rules are subject to different interpretations. The more senior members have a conservative interpretation, while the more junior ones have a more liberal take (rule: MDs should not endorse health products; I was defending unpaid skincare/cosmetic reviews are not unethical if done well, but it was shot down). As derms, we are one of the best suited to provide context and free skincare tips. They partially agreed, but insisted ALL branded content - paid or unpaid - is unethical. I explained there were so many angles to sponsored content but they wouldn't accept it so that's that 🤷🏽♀️
Hey Erin, I DMed you but will park this here too. Thanks for sharing more details on the example situation you had in mind. It can be hard to tell if there was room to improve your execution, or if there was no chance your audience would have budged regardless. It’s so situational depending on the logic and narrative of the argument itself. I’ve had clients say they made a strong case, and when they told me, I pointed out areas to improve and they agreed upon seeing it with fresh eyes. Anyway I’m happy to be a gut check to see if there’s anything I’d frame differently if you would find that helpful. If so, feel free to share what you said and how you made the case.
Wes thank you so much for taking the time to dissect the situation. Yes please, a 3rd party POV is very welcome. I appreciate your insights very much.
Hey Wes! Reading your newsletter makes me feel seen as an operator and a manager.
Today’s post is so apt cos I really felt like I was under heat earlier this week. Thank you for sharing. This perspective is everything.
This means a lot, thank you Wamide. What happened earlier this week and how did you respond? If you’d do anything differently, how would you respond now after you’ve read this?
Wow this is such a new concept to me. I viewed defense in any context in a negative light but these tips have changed my perspective. It is possible to defend in an effective and productive way that educates the person who’s asking. Great piece, Wes!
Love this article and I did came across with this many times in my career. Great to know I've done it the right way and thank you for sharing some tips.
When folks challenge your thinking, be sure to accept the challenge and take your oint if view to the next level. Always have a prepared speech or document available to support your views. Never just say stuff to impress folks, coz what you say may be challenged, or even worse implemented without inspection.
Disasters happen fast and easily. So always be prepared for negative comments and have a positive response ready. Know your work and be prepared to do a little extra to convince others if your worth to the team.
A great read and learning, Wes! Being a new manager and trying to change multiple cultural aspects of our org, I do come out strong and need to work on my skills. I acknowledge the gap here.
I’m going to be reading this post multiple times over to truly understand and implement this as a default approach rather than occasional.
However, one other scenario, which I hope you cover eventually, is when the other person is being defensive and how do we resolve those situations. Not sure if you’ve already shared one before (I’m a recent subscriber).
Always great reading your posts and I do make sure to share a few with my wider org on Slack.
There's an extreme to be avoided here, though, which is turning every dang exchange into a Lincoln-Douglas level debate. Sometimes 'thanks for the feedback, we'll consider it' actually is the better response, and sometimes 'ok boss, will do' is the best response. Not always by any means -- context is key.
oh - I guess you already addressed this in the 'insecure vibes' post. Should have read the other comments before posting!
Agreed. You don’t need to play defense every day, with everyone. A quick answer might be right the majority of the time and there is a risk of going overboard/overcompensating. Like most things, it’s rooted in exercising judgment about your unique situation, reading the person/setting, etc. On a related note, you might like this post on “question behind the question” with examples of when you might want to give a short vs more thorough answer. https://newsletter.weskao.com/p/question-behind-the-question
Think of it as them opening up to your idea...and take advantage of it.
I can relate to this Wes. After 20+ years as a leader, executive, consultant & coach, getting questions is just par for the course, and not always positive ones.
I reframe this as being asked to convince them.
Otherwise they wouldn't ask.
So many gold nuggets in the post but I really liked: "if you explain yourself well, you actually build MORE trust"
Sometimes a Q&A exchange is much better to explain things well, certainly in more detail. And trust building is a wonderful bonus.
Finally, it doesn't have to be confrontational, regardless of how the question was asked.
When they see you not taking offense, you disarm them 😉
Hi Wes, thank you for writing this article. I loved the lesson here and find it valuable. I agree with you on showing and not telling.
Contrastingly, upper leadership has made comments on my rationale like, "Get to the point. This is too tactical. My time is valuable," when I explain an important decision with my work.
Do you have any advice here?
“Get to the point” is one of the most common things senior leaders want folks to do. The challenge is it’s extremely situational what is considered too much context/too tactical vs the right amount. Could you share an example? 1) What was the context/purpose/nature of the meeting where you were presenting and talking about your work? 2) How much did your audience of upper leadership know about this topic? 3) What did they ask you and why do you think they asked that? 4) What was your response? With this context, I can better understand where you might have shared too much detail or the wrong kind of detail, and potential takeaways to keep in mind in the future.
This was so timely. I normally like to provide long-form answers when my performance is being questioned, however, I learned from others that this gives the appearance of ego and eliticism. You have restored my initial belief and helped me to once again follow my gut. Thanks, Wes!
Glad you brought this up, HS. A long-form might be appropriate, though I wouldn’t say it’s the default. It also depends on what you consider long-form. In general, I would avoid monologuing for more than a couple minutes before getting some initial feedback on whether you interpreted the question correctly. The biggest risk with diving into a long answer is it can come across as defensive. Check out my post on insecure vibes. Basically you don’t want to seem like you’re overcompensating. If you answer directly (“yes,” “no,” or one line), then share more, this can helps keep your answer focused too. https://newsletter.weskao.com/p/insecure-vibes-are-a-self-fulfilling
FWIW I also tend to answer in more long-form. I think it’s a personality thing. Some people default to answering with short replies even when they should volunteer more context. And others are the opposite. If I’m writing a reply, I like putting my main point at the top, then splitting out the context below. This gives my reader agency so they can keep reading or if they get it/agree early on, they can stop reading. But I generally like volunteering more context because I believe these are opportunities to share and reinforce my team’s strategy, what we are focused on, etc, which builds trust.
I find it very hard to not cross the line between defending and being defensive.
I found that sometimes, your best move is not offense/defense - it’s to take a timeout from the game.
In the examples you shared, the resistance was ‘soft’, and didn’t really endanger the protagonist’s idea/point of view. When some one in authority really questions your idea, and tries to push for a different course, it’s much harder to not get emotional and defensive.
The tips here are golden, and they cover just a single exchange, not the back-and-forth that usually follows. I think it’s for a good reason - after defending my idea, I found it works best to just let it sink in. Often the other side won’t be willing to let it go just because of ego, but when they cool down, they will.
I had multiple cases where senior leaders pushed against an idea, I made my defense and we took a break, and then they came back a few days believing it’s their idea… which is a huge win once you learn to let the “it was mine!” go 😂
I’d love to cover a situation where there’s back and forth that questions an existential premise, Anton. I’ve encountered this many times as I’m sure most folks have. Most discussions/debates on big decisions happen over multiple conversations, sometimes over months. It’s hard to think of a specific example now that those moments have passed though. Also I can think of some potential examples from my work, but they require a lot of context that’s specific to my startup, an issue over time, new information layered in at various phases that changed the situation, stakeholders involved, the anxieties of those stakeholders that changed over time as we got new information from the market, the evolution of my own thinking due to further thinking and/or discussion, etc for a post to be easy to follow for readers. Do you have an example that comes to mind? I’m hoping you do and are willing to share! 🤞
I have a current example one in mind. It's not perfect, but it can work with not too much context:)
Some background:
I'm a director of engineering, leading 2 small engineering teams.
We work with a single product manager, who report to the VP Product.
Our business is in the AgTech industury, which is seasonal.
Our application is heavily used in May-July (the peak of the agricultural season),
and then for 9 months we develop the next version.
Until now, we work with a 'feature roadmap'. The product and executive team
decide what we should work on, and then we develop it, usually spending 1-3 months
per feature, without any validation.
Recently, with the AI hype, we were stopped in the middle of working on a feature I believe in, to work for a new 'AI assistant feature'. Because of the seasonal nature of the business, we were told we have only until the of July to finish the project. We designed the solution, and it's a 2-months project.
Together with the PM, we offered a quick (2-weeks) product that will provide all the capabilities by will require manual work (imagine someone manually prompting ChatGPT in advance). Initially it was shot down, but after I let it go for a while (hence the advice in my comment) the plan was accepted.
And here comes my main problem. I wanted us to use the 2-week version to validate
our customers actually WANT that feature, and then decide whether should we work
to complete the other 6 weeks.
I was told we would do it no matter what, as we always did. There is a solid explanation
(we believe in that feature, if it won't be adopted well we will iterate on the way to adopt it, we need this feature for a funding round), but the problem is it's the same for all the features.
The VP Product & CEO generally agree we should have a validation phase once
I have conversations with them about it, but in reality, the just dictate which
features they believe in.
Thank you for taking the time to share this Anton. I’d want to percolate on this a bit more to see where this example would fit and for what topic. It’s probably not possible to remember the back and forth debate around what to do before you and the team landed on an answer. My initial main takeaway from this is sometimes senior management does what they want to do. I have experienced this many times too. But then what’s the lesson? I’d need to think about it more. Regardless I very much appreciate you for sharing here and in the past! Your comment in my finesse essay about how you said “all the data from the past 2 months is wrong” was so perfect. I was just telling folks about your story even yesterday.
Thank you Wes. Yeah, I can understand why the example is not a great fit here. My main lesson from it was that sometimes to get your idea to hold, you need to let go. When ego gets involved, no matter how good your offense/defense, it won't get through.
And I'm glad the other comment proved helpful! I think about that finesse article quite a lot :)