Work Besties Who Podcast

The Power of AND: Embracing Opportunities in Leadership & Life with Sarena Diamond

Work Besties Who Podcast Season 2 Episode 64

In this episode, Sarena Diamond takes us inside her journey from corporate leadership to personal empowerment. She opens up about navigating burnout, the hidden costs of “corporate trauma,” and the courage it takes to redefine success. Sarena highlights why effective change management is rooted in people, not processes, and how leaders can create supportive environments that prevent disconnection. Her story is a call to action for anyone looking to embrace career transitions, balance ambition with well-being, and take ownership of their destiny.

Key Takeaways

  • Career transitions are about defining your version of fulfillment.
  • Burnout often stems from energy drain and misalignment with values.
  • The “Power of AND” shows us we don’t have to choose—multiple paths can coexist.
  • Leadership isn’t about cutting—it’s about fueling growth and empowerment.
  • Change management succeeds when leaders focus on people, not just processes.
  • Dreams only matter when you turn them into actionable plans.

Contact Sarena Diamond at:

Website:Diamond Solutions Group, LLC – Turning "What if?" into "Way to go!"

LinkedIn: (35) Sarena Diamond | LinkedIn

Instagram: Sarena Diamond (@sarenadiamond) • Instagram photos and videos

Facebook:Facebook


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Work Besties! Theme Song Written by Ralph Lentini @therallyband

Jess K:

If you look success on paper but feel exhausted, disconnected or feel like you're living somebody else's life. Serena Diamond is here and she's been crushing it for 30 years in the corporate leadership. She's had the titles, the achievement, but also the burnout and the drama that came with it. So let's continue to talk with her about how and where she made her boldest move and how she rebuilt into something else.

Claude:

Let's get right into it Hi. I'm Claude and I'm Jess. We are corporate employees by day, entrepreneurs by night and work besties for life.

Jess K:

Join us as we explore how work besties lift each other up, laugh through the chaos and thrive together in every industry. Work besties, Welcome. We're so excited to have you.

Sarena Diamond:

Thank you so much.

Jess K:

As I mentioned in the bio, you've had a 30-year corporate career. What pushed you to walk away from that?

Sarena Diamond:

and start this new adventure. I loved every minute of the work that I did in Accenture and Pepsi and IBM, loved all the things that I learned, but at the end of the day, I had a bit of corporate trauma, much like many people that were surprised at giving your all to some place that it wasn't supposed to be. And post-IBM, I spent a six-month engagement period of time and I decided to go out on my own to really be able to work for the one boss that I could always trust, which was myself, and I have never looked back since then and there is nothing I would ever do to go back at this point. I will do this for the rest of my career because I absolutely love having control of my own destiny and my own life and my own experiences.

Jess K:

I love that. I think that's one of the things that we love most about our little work besties community is that we get to be our own bosses. It's a very freeing experience.

Claude:

It's not that easy either. When you work for someone else, you know that you're having a paycheck.

Sarena Diamond:

That's true. You go on vacation, you have a paycheck Right and it is. But there is also the aspect of you have no control over what it is that you're doing. There's a lot of years I was a single parent working at IBM and I would say, well, they didn't make me clean the men's room today.

Sarena Diamond:

And I mean I was a senior leader and doing some pretty difficult jobs as dictated to me by corporate leaders that were more senior than I was. They weren't things that I would have asked of others, which is why lots of times it stopped with me as the leader. I wouldn't pass it down to my team, but the quarterly reductions in force. There was an enormous amount of trauma that came from that. I am one of those people that believes you never cut your way to growth, so companies don't grow by cutting. But it is really an important aspect of that and I wouldn't go back ever. Now I go back and I actually help leaders be better at achieving the changes that they're trying to make happen without making some of those horrible decisions that lots of leaders have to deal with.

Jess K:

What were some of those early signs that, in your career, success wasn't aligned to your well-being?

Sarena Diamond:

Probably the hardest one was that I would have nightmares about things that were really horrible in history.

Sarena Diamond:

So, for example, during the period of the IBM reductions in force, where I wasn't choosing the people that were being reduced, I was just trying, I was figuring out how do you solve for that client commitment that we made when you're going to remove those people from the IBM workforce. I actually had a period of about three months in that job where I had that resembled Schindler's List and the gas chambers from some of those, because that's what it felt like Unbelievable kinds of trauma that was the people in the position to be removing human beings from their jobs, rather than finding other ways to solve for corporate decisions. Because, let's be clear, there isn't a layoff that ever comes without having made poor leadership decisions. I truly believe that you can anticipate well, maybe COVID made some resistance. You, as a leader, have a responsibility to be able to read the room and read the directions, and not everybody does it well, right, and not everybody is willing to read what they see. So it is certainly one of those challenges that lots of people have.

Jess K:

I hear you. Yeah, not to be a gloom and doom.

Sarena Diamond:

That was terrible.

Jess K:

You're seeing it and hearing it in the news A lot of companies are reducing workforce and, youbeing-wise, it's hard.

Sarena Diamond:

When I hear somebody in my network or somebody reaches out to me and says how did you do it for all those years at IBM? And I always start with what are you doing to take care of yourself? Because delivering that kind of message, there isn't a human being that's ready to do that, and if they are, they're not really human beings and if they're okay with the message on a regular basis, their heart's not in it and they really shouldn't be responsible for leading other people in their well-being either.

Jess K:

You have this kind of mantra of the power of end and what this means to you. How did that shape you and the business that you started?

Sarena Diamond:

So when I first started looking at going out on my own, I didn't really know how to find the clients or develop my own business and I was very linear in my thinking. I kept thinking, okay, I will go with this approach, or I will do this kind of a category, or I will look here. And it actually was a mentor of mine who stayed and we've become really great friends who said to me why do you keep saying, or what about? And? And that one question just changed everything, because that day I started saying, well, how can I get even more creative about this? So I literally was looking for jobs, reaching out to people on LinkedIn who had posted full-time jobs that I could do, and say things to them like I see that you posted this job and finding the right person for your company is going to take a long time if you're really careful about it. What are you doing in the interim? How about I come and help you as an interim hire? It didn't turn into an engagement, but I did have four conversations as a result of that and I like to think that I was really good luck because, as we would get closer to hiring me to be their interim fill in the gap, they would amazingly find the right person and then make an announcement within a few weeks. So I'm like, all right, I'll be here. Good luck to him for that.

Sarena Diamond:

The concept it has evolved. It started as how do I embrace and lots of opportunities, as opposed to singular thinking and feeling like if I had applied to 25 opportunities on LinkedIn, check the box I had done something really good for the day. It allowed me to open up lots of things. But what's really funny is it has become a hallmark of almost every engagement that I do with clients, almost every workshop that I deliver now, because so much of the work that leaders are trying to do is how do I do this, how do I do this, how do I do this and not how do I do this and also show up with the core values of my company and also balance what's true for me and my values, my personal values, how do I do what's expected and what feels like the right thing is at the same time?

Claude:

What is the core value of your company? So for, me.

Sarena Diamond:

It wanted to help me to see who I wanted to be working with and what kinds of companies, what kind of missions they were on Not that others are bad, it's just they weren't really interested or aligned with me. So I started looking very specifically at those kinds of companies and those kinds of opportunities. But what was more so is I've seen where leaders understand that they weren't supposed to be the big boss. I'm actually one of my very early clients used to say can't you just make them do it? I would say I can, but let's start with. Why would you want to try that? And I've had a client where I've had to remind them your core values on your website. Say these are the kinds of things that you want to be emulating and, as leaders, maybe have some opportunity. I've had a client where I said we're going to have a little bit of a mirror moment here, because you need to look yourself in the mirror and say how can you be expecting your people to be demonstrating these values, your leaders to be demonstrating these values every single day? When you were doing things like calling them in on short notice because they've made a mistake, right and you're taking them to task and people like how we do the work we do and what we're expected to do.

Sarena Diamond:

My biggest alignment really for the power of hand has really resonated with clients is everybody does performance management right, whether it's small or big.

Sarena Diamond:

Small companies do it for little, tiny bits, but large corporations, their performance management process starts with objectives at the beginning of the year and they're always these business results, these KPIs that you've met. Are you saying how they achieve those outcomes matter? Of course they do. Well, are you showing that in your performance management program? Are you helping your leaders to see that how we achieve the results is as important as the results themselves? Years of having these giant people that achieve these great sales results and are just jerks to everybody their moral compass is a question. The reality is that's not where anybody wants to work or the people that people want to do business with. That's a lot of the work that I do now with leaders is to help them to say you know what? Let's talk about how you achieve the work you do and show up demonstrating your core values leading, supporting, encouraging others to be doing the work that they need to be doing.

Jess K:

What's the most common mistake companies make when they are implementing change?

Sarena Diamond:

I tell people all the time a company doesn't implement change. A leader implements change because people make decisions Individuals in leadership roles more or less less prepared, but leaders make those decisions as to how to go forward. And leaders and the reason that's important is because leaders can always get better. Companies don't grow their own, their own capabilities, they grow their people's capability. So I always say to leaders how you're showing up from a transformation perspective, how, what are those challenges? The things that I often see is that a leader.

Sarena Diamond:

I will ask a question like how, when did this first idea come to you? We've got this grand vision. Maybe it's an acquisition, and this happened very recently. We had this grand vision we're going to acquire this smaller company and it just so happened that the leader was ready to sell and move out. Okay, great, then we talk about it, and so they will have taught. The leader will have thought about it, talked about it, and so they will have talked. The leader will have thought about it, talked about it, mulled it over, had meetings about it, gone for a run to the gym and thought about it for months, months and months and months, and then it's finally day to let people know about it and they send an email and then they're done.

Sarena Diamond:

Right, then they're done communicating. They're done because they've spent so much time in their own head building up the purpose, the value, the vision for this transformation. They forget to give people the purpose of it, the vision for it, the reason to join in and be really, truly engaged. And sometimes it's something so simple as communication. Sometimes it's really about explaining the why and understanding the purpose behind it and helping the entire rest of the organization to build belief.

Sarena Diamond:

The other thing I see leaders doing lots of times is the senior. Most leader will make the announcement or the transformation is going to be at the level of the CEO or the office of the COO, and they don't work on helping to cascade the change through each of the leadership chains. So they forget the fact that the people that are going to need to do new ways of working maybe it's adopting new technology, maybe it's a different process those people report to one or two or three levels of management, between the person that announced the change and the people that are living with it every day. And each of those levels of the organization can't really cascade the change and personalize it, localize it for their team. Right, you're always at odds. Right, the leader's really frustrated. I always get hired when the leader's frustrated.

Sarena Diamond:

Right, something didn't happen, the timing that they expected, the level of KPI that they expected. Rarely does someone say this is going to be a big change for our folks. Let's get an organizational change expert in at the beginning. I love it, but it's always much later than that. But when they do that, we almost always have to do a little bit of reset, a little bit of engagement that the people back into understanding the belief system, the understanding the why. But once we do that, we're always ready to go.

Claude:

Change is very often very scary, right. So what do you do to ease their fear?

Sarena Diamond:

What's funny is the reason change is so scary, and I help leaders to see this all the time. The fear that is there is based on the fact that, 99% of the time, the people that are doing the jobs that they're doing today don't see their position, don't see a level of comfort that they have now in the future state, and so leaders really need to do a good job of helping to bring their teams along. And that is not always a tell kind of story. Sometimes that is a question kind of story. So I have a series of questions that I ask leaders to ask of their people to help them feel like they're part of it. You have to be supporting, enabling behaviors in those new ways of working and making sure that the people that are so fearful sometimes that doesn't come out looking like fear. Sometimes that comes out looking like a whole lot of resistance it's the leader saying I believe in you and your ability to make this happen, and I'm going to be here to make sure that you succeed.

Claude:

And do you usually come before the changes so that you give a communication plan, or do you come after when it didn't work, and everybody's freaking out after when it didn't work and everybody's freaking out Times.

Sarena Diamond:

I come before and I will tell you when I come before. I've had a couple of clients in the three and a half years that were very intuitive and they recognized this was going to be a big change. So they said we need a communication strategy. They called it that. Really it was a leadership strategy around change and it was everything from how do we reinforce, how do we allow for feedback huge issue about allowing for feedback, making people feel like they are part of the solution as the solution is being built.

Jess K:

It's not always a train wreck.

Sarena Diamond:

When I get called, it's the place where it's not going as quickly or as positively as was expected.

Jess K:

Serena, you've talked a lot about change and you even said the word organizational change management. Can you define what that is?

Sarena Diamond:

Lots of people think that organizational change management is the new org chart when we've reorganized the company.

Sarena Diamond:

It's not, it's really unfortunate because, also, I will get called a lot to say, well, can you help us manage this really strategic project? And I ask them are you looking for somebody to hold you all accountable, to come to meetings and do your work? Because that's project management and I can have meetings. I can certainly do that for you. But let's be really clear that's probably not why things have gone south. Having a babysitter isn't going to make sure that everybody really believes they probably have more work than they can accomplish. I am one of those very optimistic people that believe everyone comes to work each day with a sense of wonder around what they're and a to-do list and mentally they've got a plan for what they're trying to accomplish. The goal for everyone should be at the end of the day. They leave at the end of the day with a sense of achievement and they're really, really happy with what they've accomplished. Today, unfortunately, I usually get called because it's the strategic project has gone south. The reason it's called organizational change management or organizational change expertise is that it is how do you bring the people along when you're changing the processes or the technology? There's a way of working right. There's the way people interact with the technologies that you know you're putting in a new system and you've got your new activities that you want people to do and processes, but people have to find new ways of doing that. Sometimes it is the interaction between departments, sometimes it is the handoffs between things, sometimes it is the governance and the approvals that need to happen.

Sarena Diamond:

At IBM we had an initiative that I ran. There were 16 levels of approval and it had grown over time. The sad part is, when we did the analysis around that process, 15 of those 16 people had not rejected the process. There was one place where we found that we were actually getting things held up. What that means is that we had taught all of the people in the process the right business questions to answer, so they knew that they could get everything. But we didn't need to wait for those 15 people because we'd already built that capability in the rest of the organization. People had adopted new ways of working over the length of time and now what we needed to do was to catch up the process of approvals because it was slowing everything down. You wouldn't know that if you were just focused on yep, the process is executing the way you planned it.

Jess K:

To summarize that when you talk about organizational change, management or expertise which I love that word better actually it isn't necessarily about reorganization or reduction of headcount. It is about ways of working and getting people to buy in, to understand why they're doing what they're doing and how to have more of an ownership of it and feel good about what they're doing Right. Build beliefs they're doing. Build beliefs. As you are helping through this organizational change process, how do you help address the burnout situation and help to recognize this within the process?

Sarena Diamond:

So you know what's funny. I think about burnout probably differently than many, in that if you're doing something that you love, you can do it all day long. Imagine something that you just is the funnest activity that you ever do in your life and you can do it for hours and you're like, wow, how did the time go by so quickly? Yeah, Burnout comes from when the energy of doing the things that you're doing is multiplied. The drain of energy is multiplied by the fact that you don't love what you're doing. It's at odds with who you are as a person or the values that you have. It's rarely physically exhausting work that you love.

Sarena Diamond:

One of the things that I ask you know teams to look at is are you, when you're burning out because you're spending 20 hours a day or eight? You know you're. You're 16 hours a day in meetings at work and then you're four hours a day trying to catch up on emails at the end and you're catching a little bit of sleep and a whole lot of coffee and you're right back at it. It's unsustainable. Not because you love what you're spending all that time on, it's because the energy drain that's happening from doing the things that are either opposite of what you love doing or in some cases, it is so repetitive it has an opportunity to be automated. There's a, there's a challenge there, and it's not usually in your.

Sarena Diamond:

In your, aligned to what your values are, what's bringing you joy, and so a lot of times, with burnout, I always look at other ways that you could be doing what you're doing today. Are there people that should be doing what you're doing, that are better equipped to be doing it? Are there other ways of you sharing some of that load across your team? Lots of times it's leaders, and often women leaders, who don't want to overly burden a team member or they don't want to ask for help with somebody who may know how to do something faster. But I think a lot of that comes from the feeling that they're just so responsible for all of it and it's so at odds with what they're either naturally good at or where they find their joy. What would be coaching?

Jess K:

to those women leaders because it does do right, tend to be a little bit more women leaders who do take on more of the workload. Sometimes it's I know I can just do it quicker and faster versus waiting, or you feel bad, or I feel like Burdening, you know, like your teams, with extra work.

Sarena Diamond:

I'd probably say just let's talk about this right, quit the message that you send when you take something away. I'll give you the story right. The leader had asked the next leader, second line leader, to accomplish something they had agreed on a deadline that she did. The leader knew that their direct report completely understood the expectations and the objectives and they had a lot of work to do. But there was a little bit of misalignment in how important it must have been, because the person that worked for this woman didn't get it done. Big surprise, it was due on a Friday.

Sarena Diamond:

Friday came, my coachee was asking where it was and oh, I didn't get to it. I'll work on it over the weekend. So that's what we all do. She was going to work on it over the weekend. No-transcript wheelhouse Absolutely.

Sarena Diamond:

Was the work that they were doing, something they were interested in? Oh yeah, she really wanted to do this project. She just couldn't get to it because she had all the other things. And was this something that was going to grow? Her skill set, her experiences? This was going to be a good thing for her to have gotten to do.

Sarena Diamond:

It was so when you were so emphatic about telling your team how their growth and their support and their achievement is the most important thing to you. And then you took the work away to do it yourself. Rather than burdening them with their growth opportunity, you told them that the work is still really more important than their individual development. As their leader, you were much more interested in achieving the work. It's funny because we had that conversation and she was like I never thought of it that way.

Sarena Diamond:

I said well, how do you think that she felt when you took it away? So you said I think she felt relieved. I said did she? Because she wanted to do this? The person said to me is that she perceived I'm disappointed in myself for not having been able to deliver, and so we ended up talking about how could you have done that differently. As the leader, you wanted to give her this experience. You expected she could have done the experience and she understood the work. And what we agreed was that doing a check-in midway, asking for things like what can I take off your plate in order to make sure you have the opportunity to do this really well, because I know you're excited about it and I'm excited about you delivering it, but not giving them the opportunity to achieve that.

Claude:

But what happens if actually it's a sucky project that unfortunately has to be done and doesn't improve the skill set right? What if the leader say you didn't have time, I will take it over in the weekend, so what would you?

Sarena Diamond:

This is an opportunity that I always say to people. Every single piece of it is an opportunity to automate, simplify, streamline something, Otherwise you would eliminate it. There is really truly a sucky piece of your business process and nobody wants to do it. I would be bringing everybody together and say, listen, nobody wants to do this, let's us brainstorm. How can we apply automation? What other ways can we get this work done?

Sarena Diamond:

Because what's not going to work is who draws the short straw this week, and if that's the answer is always I don't want to make my people have to draw the short straw then you've given them permission to see a portion of the business as if it's critical that you cannot automate, you cannot streamline, you cannot eliminate that there is something that is beyond the reach and that's really a limiting conversation.

Sarena Diamond:

But if you brought people together and said, listen, nobody likes doing these Excel, that's how people learned Excel macros, because people didn't want to have to do the Excel master spreadsheets. When you can bring people together and say, let's put our brains together and let's figure out other people, people smarter than within our organization, beyond the walls of what we are doing, how else could we be doing this work? We are in a time, technology-wise and process and people capability-wise, that there is anything that you can't solve with putting some smart people together and saying this is a job nobody wants to do, and I certainly don't want to do it over a weekend, and I don't want any of you doing it over a weekend either. So let's figure out how do we make it automated, how do we make it limited, streamlined, Really powerful message to people too.

Jess K:

One thing I would add to that is even if it is something nobody likes to do and you start taking on all that stuff as a leader, then you start setting the precedence that your team doesn't need to do the stuff.

Claude:

that's minutiae, because sometimes automating is not an option, unfortunately, because it costs money.

Sarena Diamond:

There are ways around that and you're right, but it shouldn't be the leaders doing it. Then the question is are there other people that should be doing it? Should we be outsourcing this elsewhere? There are always alternatives to saying I want a highly compensated, highly skilled individual to be doing something that is beneath their experience and their skill level, and they shouldn't see you doing it either, because then they learn the lesson. Whoever wants to be promoted, because all you do is get the things that you don't want other people to have to do.

Jess K:

Slightly switching topics here. You also talk about the power of what if? And you really help your leaders. You help them move from vague dreams to real action plan. What is that biggest mind shift? Your clients need to do that in part of this process of a transformation.

Sarena Diamond:

My whole tagline is turning what if? Into way to go. People say, what does that mean? And I'm like, well, everybody has that. What if we could do this? Or what if? There's always a wondering that goes with the what if? Part.

Sarena Diamond:

And then there's that aspect of that'll never work. You know, you always have the people that are the the glasses. So not even half empty, right, it's not half full, that'll never work. That'll never work. Oh, that could all. Let me tell you all the things that could go wrong if we try. They're the really cautionary ones, right.

Sarena Diamond:

And then you say there are people that would no matter what, they'll figure out a way to make it work and they'll find that positive. So I always say to, especially the leaders, when you can see it, our team could do this. Imagine if we as a group could achieve that. How do you get to a place where you are celebrating with your team, way to go, the achievements that you get, and that comes from very specific functions around building the belief in what that is? Very specifically, you need to make sure that people are engaged, communicated and they feel like they are a part of it. Then they can say, okay, I'm all in, but I don't know how to do it. So then you have to enable skills, set and enable those behaviors, and you build that, not just the capabilities in the people, but also their comfort and belief that you are supporting them in their growth.

Sarena Diamond:

One of the things that leaders struggle often with is they forget about the people. Once they see it, they may have to learn new ways of working, new things, new skills. So how do they learn that? How do you model that for them? And then, once they've achieved the most important thing is, how do you sustain this? I have a whole talk that I do around not having the work that you do be flavor of the month. It's the worst thing to know that your team is thinking well, this is flavor of the month for the boss, right? So we'll get it until the next thing that comes. Sustaining change and that era of continuous improvement is really about cultural norms that say nothing is beyond our reach. We have the ability as a team to achieve anything that we can dream up, so the what-ifs become way to go on a regular basis. And that's the important part of any kind of organizational change, big or small, is making sure that you do all three of those every time.

Jess K:

So, based on that, what does being unstoppable mean to you?

Sarena Diamond:

It actually started as a result of finding my opportunity to start my own company. There's so much in the world that will limit us to the boxes that society says we're supposed to be. For me, unstoppable really means not necessarily allowing myself to be defined by what those other people have decided was the right thing. So much of my going out on my own and learning the ways of doing business development as a solopreneur after 30 plus years of corporate life was really hard. And how do you find ways of networking? How do you find ways of talking with other people? And there's so many community build and membership opportunities out there for people.

Sarena Diamond:

I tell people find your own group that feels the most comfortable for you, allowing yourself to have time to learn from people that have come before that are genuinely and honestly interested in your success.

Sarena Diamond:

Come up to me at the end and talk, and that was the end of it. And then, a few months later, I get a message on LinkedIn that says I don't know if you remember, but I've had two of those that have happened in this last quarter where women that had seen me speak at a thing during the International Women's Month have come back to me and told me something that I had said to them. It made a difference to them, and I think about the people in my life, like Audrey, who asked me the question why do you keep saying, or what about? And? And I think about all those things where you've said something to someone that made a difference to them, and the ability to have that impact on someone else's life. That's what we're supposed to do as human beings. This isn't about getting out of another world at the end, but having won. There is no winning. That's really what it is for me.

Jess K:

That's amazing, karina. Every last question for you, because this is a work-vesting community. A lot of our listeners out there probably are asking themselves the question now is this it? What does that mean for change? So what would you say to help them take that first step towards change?

Sarena Diamond:

I would tell them to try and define what it is they want out of their one precious life, what is going to give them not just joy but a sense of accomplishment. That's the piece that allows you to say I know what I need to be doing and I need to be moving toward. And if they can, allows you to say I know what I need to be doing and I need to be moving toward. And if they can't figure it out, I'm more than willing to chat with people and ask them the kinds of questions that I ask. Love that.

Jess K:

Serena, thank you so much for showing us what success does look like, and we so look forward to partnering with you, and we'll want to say, if you could just let us know really quickly how people can find you and where to connect with you.

Sarena Diamond:

Easiest way is LinkedIn. If you spell my name right, I am the only Serena Diamond spelled S-A-R-E-N-A. I'm the only Serena Diamond on LinkedIn.

Jess K:

Remember whether you're swapping snacks in the break room, rescuing each other from endless meetings or just sending that perfectly timed meme. Having a work bestie is like having your own personal hype squad.

Claude:

So keep lifting each other, laughing through the chaos and, of course, thriving. Until next time, stay positive, stay productive and don't forget to keep supporting each other. Work besties.

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