The image features a photo of Sharon Ehrlich and Ann Jameson. Both women are smiling at the camera and wearing their hair loose. Sharon has on a light blue dress. Ann is wearing a black suite. The text reads: Sharon Ehrlich in conversation with Ann Jameson, Episode 41, How to Reframe Setback, Accept No and Get to Yes!


You’re tuned into a recording of the Living While Leading podcast, which was originally live streamed on LinkedIn. My guest today is Ann Jameson, an IT executive at a fortune 50 company.

Stay tuned as we explore techniques to reframe setbacks as opportunities for growth and share insights on how resilience and adaptability can propel you forward on your leadership path.

Find the full transcript for this discussion and other resources at

I’m really excited today because we have a guest joining us from Singapore. We have Ann Jameson with us and today we’re going to be talking about How to Reframe Setback, Accept No, and Get to Yes. Welcome to the podcast. Please introduce yourself and tell us a little bit about yourself.


Thanks, Sharon. And thanks for having me. As we were talking earlier, it’s been it’s a bit of a challenging week in terms of, an end of a quarter. I’m about to go on leave and so I do feel like if I could if I could clone myself, it would be a much easier week.

My name is Ann Jameson. I’m coming live from Singapore tonight and I am currently a senior director at Microsoft. However, I have lots of other things that I enjoy doing other than working. I have a family. My husband is Jason and my two children Thomas and Sarah George. Thomas is 13 and Sarah George is 10. So, it’s a pretty full life with two working parents. But it’s a lot of fun. And I enjoy it. I’m super excited about this topic, Sharon. So, thanks for having me.


We’re going to jump right into the questions because I have so many things I want to ask you, and I’m sure that you’re going to drop a lot of knowledge here. The first question that we’re going to start with is, can you discuss the importance of adaptability when faced with a setback, and perhaps share how that played a role in your career progression?


Adaptability is one of the most important parts of not only a setback, but in an in a career, a setback even more so because adaptability also helps you learn resilience and I do think in any type of setback or change resilience can be super, important.

Let me take it from two aspects.  From a personal aspect adaptability can allow us to understand change, how to navigate change, and to also learn to be okay with change in today’s world, no matter what you’re doing the rate and pace of change just in life, in careers and technology due to all of the information that we have access to adaptability to change is super, important.

It allows you to understand how you can navigate change. It also can, if you’re leading people, it can also be super important to help instill confidence in that team or people that you’re working with. So how you adapt and if you have resilience towards that change or even, you know, a note to the team or a setback for the team, whether it could be making not making numbers or if you have employee surveys where you might have gotten to that feedback. You know how we adapt to that and how we take that as Okay, I’m going to learn from it versus as a setback. So, it’s a reframe of that is super, important these days.


You make a really good point there and this notion of being okay with change because it’s just inevitable. It’s something that we have to deal with all the time. I do want to ask you a question, though, because you did talk about being a leader and of coaching your team around adaptability and resilience. What do you do when you have someone on your team who you just recognize is burdened by change and they need some support in becoming more resilient and bouncing back and recovering and moving forward?


It happens all the time. Part of it is you have to build a trust with your team and also recognize that, people deal with change differently. So, whether you talk about it in a group, about how people are feeling about maybe an adjustment that’s being made in a company or, somebody has to go on leave or whatever the change may be, and it’s also important to create what I call — a space or a container— of, it’s okay to not be okay with change.

It’s okay to bring it up — and I will say this in a setback or anything that that is happening—that it’s okay to be vulnerable in this position and just be able to express in any way whether it’s in written, it’s verbal, it’s a chat, it’s however anybody wants to deal with it, but it’s okay to say I’m afraid of change. From there, you want to make sure that there is a way for somebody to get underneath that so it’s taking a very unbiased or and non-judgmental approach to and also to give yourself some grace.  It’s allowed them to talk about it, and just be okay.

Let me just kind of summarize that because I think I said a lot there. It’s about the trust that you build. It’s about a container or a space or an environment that people feel okay to say, I’m worried about change. And then getting under the details. There are questions that you can ask or ways to approach it. You could have an employee that at one minute is okay with the change but at the next minute, depending on what’s going on in life personally and professionally, the change can be reacted to differently. And if it’s a setback, then it’s even more important to get underneath what’s causing that.


You said something really important there and above this container for change. I always tell my clients when I’m coaching, you’re allowed to feel your feelings. We are allowed to feel our feelings. And then there’s a moment in time where you have to say okay, I felt them and now what is the next step, what am I doing? Or how can I examine the situation and understand where the lessons are? What can I take to move forward whatever forward can mean in the context of the situation.

I want to talk to you about staying motivated because change is inevitable as we know. And sometimes change can be a setback. It can be a no to something that we really wanted. If that happens to you. What do you recommend people to in the context of having professional setback?


This is where I feel like mentoring networks, trusted advisors play a great role. Finding someone that you can actually, again, just what you said about feel the way you feel, but express that to somebody that again. I’m back to this word trust, whether it’s an advisor whether it’s a mentor, whether it’s someone in your network.

I stay motivated, because I reach out to people when I’m feeling setback, or if I have a “no” bounce that off them, because it gives me a different perspective. I think that those people are really, important and in that kind of time.

I’m an avid exerciser. So I think if we look at the mental and the physical part of a setback, you know, mental, emotional, physical, I oftentimes will stay motivated in terms of okay, I’m just going to take a step back and allow it to land and go exercise or go do something fun, that’s physical, to get all that kind of pent up energy out, and then come back to it.

A third way is I will go figure out something that I want to learn. I’ll take a break and say okay, you know what, I’m going to go research this topic. Something that doesn’t have anything to do with my job or the setback. It just takes my mind to a different place. And then I can kind of reframe things from a perspective of, okay, I’ve just done something that I want to do that is maybe it’s not mentally challenging, but I’ve just researched something a topic that I really love, and then I’ll come back to it.

I think that’s kind of how I stay motivated. I also try not to let one setback, determine how I’m going to go forward. It’s just it is just one thing. And there could be a myriad of reasons why that happens. And it doesn’t define you. It’s like a singular moment in time, as we were talking about earlier. So sometimes context is really important.


And that can be difficult when you’re in the middle of it because you’re so close to it and you have these emotions and expectations and maybe even expectations of other people. I want to ask you a question about balancing the determination to turn a no into a yes. And when do you know that you should just move on, just drop it, stop fighting the fight and just move on.


Number one, if you get the first no or a first setback or rejection or whatever we want to think about it. I evaluate why do I want to get to yes so badly. That’s my first question. Why am I taking this no so badly or really to heart and why do I really want to get to a yes. So that’s my first thing that I would look at.

The second thing I would look at then is if it was no, is there another route to yes. Is there another path? Are there other people that I need to have briefed or can help me get there? And is it worth it? And what’s the ultimate outcome in terms of getting to yes, and also being convicted to ask why it was a no to begin with?

It depends on the circumstances, or who said no. Are they open to telling you why? Is there an opportunity to get to yes? Then just evaluating the why like, why is it so important? If I am really convicted about something and it should be a yes — then I try to find a way to get there, whether it’s a different path, a different person, a different perspective. I think my limit is three times. If I’m convicted about it, then I will try to get to yes, but I think it’s important to understand individually why that’s so important. And then move forward from that space.


The why — this three-letter word that really takes a lot to peel back to understand. Why am I so fixed on this? Why does this need to happen for me to feel like my career is going on the right track? Sometimes you can’t get to the why by yourself. Sometimes we do need those mentors, sponsors, coaches, like me, or trusted advisors, and have a sparring partner because it’s very difficult to be real with yourself when you’re in the middle of rejection or setback.

Have you ever experienced a “no” that made you question the direction of your career or the values of your organization? And how did you handle that moment of truth?


Recently to be honest. It was a very difficult conversation. I did question after all the hard work after all the setup be moving forward career progression that I had done previously. I was like, oh, hang on a minute. Is this really the place that I need to be? Even though, I love my job. I love my team. It was just I did feel like it was a massive setback.

I have learned in my career, not to react immediately. Again, let things land and that comes from experience, and then try to peel back the why. And oftentimes, it’s not because of you personally. And it’s not a performance piece. It could be something politically that’s going on in the business. It could be a change of leadership. It could be those conversations that you were having before have changed because a leadership change happened.

I had to take stock and evaluation and understand okay, this is not going to be my only opportunity to move forward. I trusted myself, I trusted my capabilities. And actually, it allowed me to begin to look more broadly at new roles and new opportunities.

And when there’s a setback, I’m always in learner mode, I kick into hyper-learner mode. Why did it happen? Is there an area of opportunity for me to change and or is there a broader opportunity externally. Meaning the current situation that can then lead to a better opportunity that’s more aligned to where I want to go and to begin with? It wasn’t necessarily about title. It wasn’t necessarily about a bigger team or any of those types of things.

I’ve experienced to number one to let things land and not to overreact. Don’t get angry because that can create resentment, but really take stock of what else can I do and why? Because it could be a leadership change. It could be politics. It could be other deck chairs, or other pieces needed to move. And it just was not the right time.

I use my network and I use my trusted advisors to advise, but it also is being super vulnerable about how I was feeling and then calmly and rationally working through that and back to your point of it’s okay to feel the way you feel. It’s just how we react to it and how we begin to again reframe it to say, okay, this is not where I wanted it to be. It’s not a good thing for me right now, but I’m going to channel my energy into, the next time or the next opportunity that that I can take on.


You’re probably familiar with the phenomenon that’s going on where there is a lot of organizations are experiencing retention problems. Where employees become frustrated one for one reason or another mostly for how their careers are progressing, and they just sort of throw in the towel and they walk away. What words of advice would you give to our younger listeners here who probably are confronted with a career path that’s not the one that they actually imagined? Maybe it’s not tracking as fast as they thought that it would. It’s not taking them exactly where they want to be, but the timeline they want to see it. What advice would you give them to react as opposed to just throwing in the towel and walking away?


I always give this advice to anyone that I either mentor or on talking to it’s on my team or somebody who comes to ask me about career development and progression. Number one, I think you got to understand why do you think you should be progressing faster?  What are the criteria in terms of progression in our head? Sometimes we feel like it should be progressing faster, but why is it not right?

You have to be real with yourself. Then figure out where you want to go and go ask for it. Don’t be afraid to ask for what you want. I’ve always had that mantra. Be prepared that it may not come to you at that moment, but never give up asking for what you want. It’s that conviction.

One of my really great mentors said you can’t be the princess all the time and you’ve got to kiss some frogs, meaning you’re not always going to be tapped for your next role. Sometimes you’re going to have to go out there and seek it.

So, if somebody is not giving you that opportunity, be convicted, understand where you want to go and then go ask. Keep asking. It’s that really kind of self-actualization of where did you really think you were going to be at this point in time? Why do you feel like it’s not moving as fast as you want and then if you can answer those and satisfy those, go find somebody that will give you that opportunity. But be very clear as to why you should be given that opportunity. So, when you come to ask for it, it’s very clear why you should have it.


There is a degree of preparation one needs to take in order to have that conversation, isn’t there? You just can’t, kick in the office door and say, hey, I want to talk to you because I need to be here and I want to understand how I get there.


And it’s not just okay to say I’m two years in a role, I’ve learned everything, I’m ready to go or I should be promoted, or I should be moving on. Timing happens not only in our own time, but the time that the company or the person that’s hiring is ready to go. So, timing plays a critical element.


Can we talk about the positive side of “no” because not all no’s are bad. Can you share a time when you had a no that led you to a better opportunity? And how did you navigate that transition?


I was in a position that I was recommending a new position. And this is a previous, not my current role. I could very clearly see the need for customer success and how we could form that group. I did a pitch that said we need this team. We need to have these people in this position because it’s going to be good for our customers and in particular, as we look long term, where technology was going where the cloud was going, where AI was going at the time, I could just so see it so clearly.

I went and did this pitch to one of our fellow execs and the upper-level exec said, well, we don’t have that position. And I was like, so you’re telling me no to a great opportunity to create a great team for our customers, because we don’t have that position. And for me, that was a setback, because that’s the path that I wanted to be on. And I was so clear that it was the right thing to do.

I was in line for, a vice president position and I was not going to go for it. Because I thought if this group cannot see my vision and can’t see how this can really help the company — I don’t want to be with that company anymore. And I can’t sign up for an upper-level executive position.

I was like, oh no, what do I do now? This was my path. This is what I was going on. In fact, the question before, I know this is what I’m supposed to be doing. I know that I should be moving into this role. I have a lot of emotion around that and how I said I’m not aligned to where the company’s going and the strategy.

Yes, I could have pursued the vice presidency and kept going but I didn’t. And then all of a sudden, my opportunity came up to go to Microsoft, and I’ve never looked back. It did feel like at the time, what was a step backwards, but in retrospect, it was like 10 steps forward, because I’m so aligned to the culture where the company’s going, the way that Microsoft looks at a growth mindset.

That no allowed me to open my eyes to being willing to change companies. That one simple no change my career full stop for the better. Even though at the time I was like, are you kidding me? Like you can’t see this clearly. Because it was so clear to me. That’s when a no became a career changer.


And can we talk about advice you would give to your younger self? Now that you have the benefit of all of this lived experience and so much of a career behind you but still a lot of career ahead of you. What would you tell your younger self?


Number one, don’t worry so much. Number two, trust the process, and align yourself with people that you trust, trusted advisors, and you have to nurture those relationships. It’s not just a one-way ticket. It’s really important to reach out to your network, build your network, get back to your network, and that it doesn’t have to be a linear path. You may take a sideways step, you may take a step up, you may take a step backwards, but if you’re learning something and you’re growing and you’re building skill that’s applicable across areas that you like, then that’s a good thing.

I also think I would tell my younger self, be passionate no matter what you’re doing. If you stop being passionate about it, then it’s time to change and really evaluate what that change looks like. My younger self I was a perfectionist. It was really hard for me to not have everything perfect and lined up and here’s my next role. And step one, step two, step three versus really having a growth mindset and looking at all angles.

Building those trusted advisors and aligning yourself to that and also you’re going to get no’s along the way. And those can be lifelong learning lessons that can take you forward and back to our original question. Building adaptability, building resilience. I would just tap myself on the shoulder and say you know what, it’s going to be okay. You’re going to be fine. Don’t worry.


I think one piece of advice I would give my younger self is not to take it all so seriously. Every single decision just seems so consequential that took some of the joy from things and I’m not saying that you should take your career lightly. But on the other hand, not every single moment is consequential and it’s going to change your life that significantly.


No decision in a career perspective is forever. You can make a change if you want.


I wanted to talk a little bit about something that you mentioned with relation to the mentors and the sponsors and the trusted advisors. And you said that’s a two-way street. I think it’s worth highlighting that those relationships have to be cultivated and it’s a long game and it’s a give and take thing. Do you want to add anything else to that?


Well, it’s just like any relationship, whether it’s a mentor or a mentee, a trusted adviser, someone that’s in the office that you might be having a conversation with. It is really, important to continue to cultivate or to check in. It doesn’t even have to be a long conversation. Hey, how are you? I had an executive coach when I first joined Microsoft, and I still talk to her. It’s not every day, but I want that relationship to just continue longer term.

It doesn’t have to be a long conversation and by the way, it doesn’t always have to be a career conversation. It can just be hi, how are you just checking in. But you do have to cultivate it, that cultivation can’t be forced as well. Like I think people say go find the mentor, go find the advisor, go find somebody to talk to it’s just like any other relationship in your life. You’ve got to trust the person there has to be chemistry you have to get along you have to be aligned, but that as you say it takes cultivation in a big way.

It is important that you give back as much as you get.  You pay into it as much as you take out of it and it’s important to keep that equilibrium. I find it super rewarding if I can take something from the network as well as give back and there will be always times that I may need to give more at a specific point. I will take more at a specific point. It takes work and you have to work at it and set aside time even if it’s just in a diary for the day. Hey, drop a quick email to say hi to this person or you know what I haven’t caught up with him for a long time. I was just talking about this over the weekend. I had a really amazing mentor that I haven’t talked to in ages. He’s retired and I do need to reach out and for no other reason just to say hi and check in.


I can’t believe how quickly the time has gone. We are actually out of time. I’s like to thank everybody for joining us live and for those who are listening to the replay next week, I’m thanking you in advance.  you’ve been an amazing guest I think that you have said so much and this was really a valuable mentoring session for everybody who has listened to who will listen. Please feel free to connect with me and Ann on LinkedIn. So again, thank you everybody for tuning in and have a great rest of the day.