Transcript

[0:00] I think one thing about this is there is part of change and part of communicating change that sometimes goes into, I want to make everybody feel heard and I want to make everybody feel like they can make decisions.
And that can very easily backfire because the reality is not everybody can make decisions all the time.
There are things that you can influence and you can co-author when it comes to change.
There are things that are decided and need to be that way.

Leading Change Efforts

[0:31] Welcome to the Full Funnel Freedom Podcast. If you are listening to this, you are likely leading a team responsible for generating revenue.
Purpose of Full Funnel Freedom is to support people like yourself and keep your.

[0:43] Music.

[0:44] Funnels consistently, reliably full.

Guest Introduction: Roberta DiGiuliamo

[0:49] Welcome to the Full Funnel Freedom Podcast. I'm your host, Hamish Knox.
Today, I am delighted delighted to have Roberta DiGiuliamo, Director of Sales at Dropbox, as my guest to talk about change management.
Born and raised in Italy, Roberta spent the past 12 years living and discovering multiple countries, including France, Australia, Belgium, Ireland, Texas, and now she's based in New York, learning about how cultural differences influence the way we operate.
Roberta started her career in the public sector and quickly pivoted to tech sales following the advice of a wise mentor.
Since then, she has covered multiple roles across direct sales, sales strategy, and operations, and now in sales leadership.
Roberta, welcome to Full Funnel Freedom.
Thank you. Delighted to be here as well.
Delighted to have you as a guest today. You are our first Italian guest on the Full Funnel Freedom podcast, so I'm delighted to have you here with us to talk about change management.
Before we get into that, I've given the audience like the 30,000 foot view of who you are in your story.
Take us down a level. Tell us the story of Roberta and how you got from where you started to where you are today. Absolutely.
Thank you. And perfect pronunciation of my last name. I know it's a challenging one. Thank you for that.
So I think you covered a little bit of that. My story is a story of change. I try with change.
I've been moving across different countries since I was very young.

[2:14] You mentioned a mentor told me to go into to sales the story there is a little bit different i've actually heard a lot of people in your podcast saying the same but i stumbled upon sales by mistake it was by chance my mentor told me to go into tech um what happened there was somebody reached out to me and i knew nothing about sales and i very quickly learned that i loved sales and i think it's because sales has that element of constant change being the driver of success you always talk to different customers different different industries, different businesses.

[2:50] Problems you're dealing with. So you're always adapting to different conditions that changes the constant there.
So that is what really I found entertaining since the very beginning.
I was a PDR, I was in direct sales, and I love that.
You say that I moved into strategy and operations, and I took the lateral view of sales, and it really helped me understand from almost a sideline, what is driving sales from a different perspective.
And then I leveraged what but I learned that to go into sales leadership.
And that's what I do today. I lead multiple sales teams.
And I keep talking about change.
I care about change because I feel it's such an important part of people leadership.

[3:31] And sales leadership is people leadership.
Amen. And I love this idea of change because we tell our clients, no matter what you sell, you're selling change.
That's ultimately what it is. And humans fear death, taxes, and change. age.
So this is a challenge because we're going out and trying to sell to someone who's like, I would rather not have to change at all, even if I have to change only one degree to the right.
So help me understand what causes you to really enjoy change because most people don't.
So what is it about change that really ignites your passion?
I love that you say that because it's exactly the same way I look at a change when it comes to sales.
There is change that is impacting my sales team and those are things like structural, And then there is the change that is driven by my sales team, the one that you talked about that is impacting our customers.
What do I think is good about change?
Change in the ideal case scenario is driving towards something better.

[4:30] People most people don't like about change is the fear of loss what are you losing that is coming with change and sometimes we forget how important it is when we talk about change we focus all on what is good that is coming from sales from from change um and we let go of the element of there are going to be some things that we have to let go as part of data so i think coming to peace with the fact that that is part of change and it's something we have to accept being intentional of the way you think and you talk about what is what is we're losing through the change is what helps me look at it in a positive perspective all the time that is super cool because you're right there is this loss and and and we forget as leaders that our people are not robots they have emotions and we've gone through those emotions when we started initiating the change wherever that was before we we rolled it out so if you were coaching a sales leader to to walk through this idea of helping their team overcome this idea of loss, whether it's a change in comp plan or a change in territory or whatever it might be?
What advice would you give to a sales leader who's got to implement the change and they need to help their team through this sense of loss?

[5:41] When we think about change, there are normally two elements.
There is the status quo, so before change, and there is what's coming, the after change.
Change and in an extreme case and obviously there are shades to that but both the status quo and the future status have some positives and some negatives and a lot of people again focus on these are all the bad things that are happening today and this is all the good things that are happening in the future and what people immediately think about is uh.

[6:13] These are some of the, like, my manager, the person who's communicating change is trying to gaslight me into this very positive scenario.
But these are all the good things that are happening today that I'm going to lose. And these are all the negative things that will happen in the future that will impact me negatively.
So my first advice to somebody who is coaching, who is leading their team through change will be to be intentional about how you communicate the negatives as well.

[6:37] First of all, I would recommend starting with what's positive today that is staying.
Not all of what we're changing is gone so what are the things that you can keep in that are making you successful today that are going to stay there and being vocally intentional about those because sometimes we forget a good example of that for me is um in sales if you're changing a territory it's a big change reps gets nervous about that what are you keeping are you keeping your pipeline are you keeping your bdr what is staying the same that is supporting you that you have found success with and be intentional about communicating that.
The second part of that is calling out what the potential negatives are in the future as well. We know that those are there.
It's better to discuss and share what those look like so that you can be complete about the vision you're picturing of what is happening today, the positives that are staying, the negatives that we're trying to solve, and then what's the future, what are the positives we're going to bring, but also these are the risks and the negatives that we are expecting and we're going to go through that together.
Beautiful. It's balance, right? That's what I'm hearing. is it's not like it's not everything is changing not everything is staying the same we we want to make sure that we have that clarity and conviction in hamish you're still keeping your pipeline or you're still keeping your bdr or whatever that might be so once we start rolling out a change because also as leaders sometimes we get in our heads like oh i'll just announce it and everything will be wonderful and you and i both know that's not the way it works so as leaders are managing change.
So we've launched it. Great. Team understands.

[8:04] How do we keep that change rolling from your perspective?
So we get to the ultimate mountaintop that we're trying to hit with the moving around that's going to be required because we've got human beings in our organization.
How do we keep that change going? I am thinking back. I think Simon Sinek had a very good video where he explained something similar.
Whenever you're implementing change, there is this Gauss curve of you're starting really low, you're going really up and you have different people that are reacting to change in a different way, along a timeframe that is different for everybody.
So the first thing I will recommend is being.

[8:45] And understanding who in your team is going to react to change in a different way.
There are always going to be the early adopters that are going to be excited about change, that are going to be the advocate of change, that are going to implement what's changing, and they're going to see the first results of the change.
Those are the people you should actively speak to. Those are the people that you should bring into your pilot teams.
Those are the people you should bring into your, when you're formulating change and co-authoring change.

[9:10] Those are the people that are going to make the difference. And then there is going to be a big part of your team or the population that is going to kind of be curious about change, but scared about what the impact is going to be on them.
So they're going to sit and wait and look at what is happening among the rest of the team before they're making that step.
And then there is always going to be that low tail of people that are always going to be a little bit skeptical about change.
They are scared that it may be a personal predisposition and maybe because of the way they have dealt with change in the past, they are going to have a negative attitude towards change.
So you need to make sure you are intentionally communicating to these different groups in different ways.
If you get these people into a pilot, they are not going to be excited about the potential of change.
You need to be intentional how you're choosing people and at which phase you're bringing them along.
And then if you're doing that correctly, the people that are going to start with the change are going to bring along the big piece of the population that is in the middle and waiting for change to be proven effective.
And then you're going to have most of the team. You're never going to have all of the team being positive about change or implementing change immediately.
But the moment you have the vast majority of your team being there, you are all the way there.

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Successful vs. Unsuccessful Pilots

[10:57] I love this idea of pilot. Let's talk a bit more about pilots from your experience, whether as a leader or as a, as a, as a rep, what have you experienced in terms of really good pilots?
And then also conversely, what have you experienced maybe with, with pilots that didn't go so well?
There are some elements of a pilot that will make it successful or not successful. And, uh.

[11:20] I'll start with the success for a pilot. It's not necessarily we've proven our point, right?
A successful pilot may be we've proven our point wrong and we need to do things in a different way. That's success.

Pilot Success Factors

[11:32] What I consider a not successful pilot is a pilot that didn't achieve the goal of understanding what we're testing for, that made people scared about the outcome, that made people scared about change because of the way it was structured.
So some things to keep in mind for that is being able to be safe in the way you're experimenting.
You need to make sure that you are considering what people are, again, losing with the change versus keeping with the change and creating a system around it, a framework that is protecting the people from the outcome of the pilot.
Because the outcome of the pilot may as well be negative. And that's a completely fine outcome. The second part of that is really starting with a point of view on what you're testing.
If you are going into piloting and you don't know exactly what you're piloting or what you're testing, you're going to try different things that you're going to move too quickly.
You're not going to be able to go back and understand what's being tested and whether that's successful or not.
And a side note to that is also you do want to make sure that you have a good data-driven system in place that doesn't need to be absolutely extra complicated.
It can be very simple, but you do need to have some metrics in place that tell you your pilot is successful or not successful.

[12:45] And then the third part of that is the feedback loop. Super important.
That can be quantitative or qualitative, but you need to make sure that you are collecting that feedback continuously throughout the experiment, throughout the pilot, to understand what you need to adjust and then make those adjustments along the way.
Brilliant. It's the scientific method. I have a hypothesis.
I'm going to run an experiment. I'm going to get data. And as you just identified, the worst experiments are the ones where the science is like, I want this outcome.
And if I don't get this outcome, I'll manipulate the data to make it that outcome.
And so instead, we have to be open to whatever the possibilities are.
And maybe we find out that we're wrong.
And that's a good thing. As you said, it's successful. So let's move on from successful pilots. So we run a pilot and it works.
Then what's the next step? Because pilots sometimes are the whole change and then it dies.
And it was like, well, why did we bother even doing that? So where do we go from a successful pilot into maybe a more formal change role?
That's a very good point. And I've seen that over and over, actually, with experiments or pilots that have lived their course of life for a few weeks or a few months or even a few quarters, but then nothing happened after those, even though they were proving successful or starting to show some success.
I think that depends on being intentional on the planning phase of the pilot, on what are you defining as a success rate criteria and what is happening after that success criteria is met.

Transitioning from Pilot to Formal Change

[14:05] And those are things, for example, if you're running a pilot where you are expecting to to increase productivity for a sales rep.

[14:12] You want to make sure that you have included into the hypothesis and into the planning phase of your pilot at what point we are expanding the headcount that this pilot is including.
At what point are we adding and what are the measures of that?
It goes back to the data part of the pilot of I want to make sure I am a priority thinking about what those numbers look like so that I don't have to make the decision in the future when we don't know if things are different.
We're not going to have those metrics to guide the decision.
So it's going to be based on more subjective criteria than objective based on the pilot results.
Let's look at that human side again. So we've talked about how we've got the people who are like all in from the beginning.
We've got the fence sitters and then we've got the people who are maybe going to get on board, but it'll be later. Maybe they'll never get on board.
So as a leader, you know, we don't ever want to have to fire somebody or move someone to another team because we hired them for a reason.
And we're also making this change because it's gonna benefit not only the company, but our team members.
So how do we walk through that process as a leader with someone who is just digging in their heels, they're turned into a donkey, they're never gonna get on board, and we have to tell them like, this is the new reality and I love you, but you might not be part of my team for very long. As a manager.

[15:33] To me, it goes back to understanding motivation. How do you get to the why?
And there is a why to everything.
I think I touched on that before, but some people are resistant to change because they had a similar experience in the past or because they have experienced the change being communicated to them as a positive when in reality it was a repackaging of the status quo or it was negative change for them.
So as a manager, you should have that connection with everybody in your team to being able to have the conversation around the why and the motivation that is driving the behavior of your team, understanding where that is coming from, and then get on a journey together to work towards removing that cause or changing or making sure that you are supporting your team or the person who is resistant to change as needed.
It's not always going to be possible. And I think every conversation between a manager and his team is a conversation about negotiation conversation where the manager comes from a place of how can I help you given these are the things that we need to get done.
So understanding what cannot be a decision for the rep and what are the things that the rep can decide instead.

[16:44] I think one thing about this is there is part of change and part of communicating change that sometimes goes into I want to make everybody feel heard and I want to make everybody feel like they can make decisions and that can very very easily backfire because the reality is not everybody can make decisions all the time.
There are things that you can influence and you can co-author when it comes to change.
There are things that are decided and need to be that way.

[17:10] So I think being honest about what can be decided and what cannot be decided is also part of that. True.
As leaders, our number one role is to create clarity with our team.
And if there's something that is non-negotiable, to use that phrase, then it's non-negotiable.
And as a seller, you can make a choice whether you want to stay or whether you want to go based on the fact that as much as I might want to change it and you might want to change it, this is the way things are going to go forward.

Handling Resistance to Change

[17:39] Let's dive deeper into this idea of getting connection with your team, because I love this idea, something I coach my clients on, around having that connection so you can have a clear, direct conversation about change and why and motivation.

[17:53] How does a leader develop that, especially in this day when a lot of us are managing our teams on video?
Great question. I actually, my first manager role started basically at the same time as the pandemic.
So I have, for a very short time, managed a team in person.
That was interesting because I thought I was going to miss that in-person connection, the idea of building that in-person connection with my team.
However, I think it really helped because it made me a lot more thoughtful about the way I'm trying to be proactive and connecting with my team than I would have been if we had that, you know, surface level connection that you can have when you're in person, but you are not thoughtful and intentional about the way you're building that.
You're getting to know your team. In terms of how to build that connection, one of the first books I read when I started as a people leader was Radical Candor.
And there are a lot of concepts in the book and some people are supportive, some people are not.
One thing that really stuck with me was the idea of deeply caring about your team.

[18:53] It's the idea of as a manager, as a people manager, your job is to deeply care about the success of your team. And you cannot care or you cannot influence anybody's success unless you understand what their motivators are.
I think that means being vulnerable to a certain extent.
It means asking questions that are outside of the pipeline and deal management and deal review.
And that doesn't mean you have to ask questions about like, what are you doing on site? Or they're like personal questions.
But it means that you have to go one level deeper around why do you want to be successful? Why are you in the job you are in today?
What would drive you to sales? What success looks like for you?
And then digging deeper into those questions, I think I'm going down the pain funnel almost of understanding, like removing the layers of the onion and understanding deep down what is really motivating this person and how can I help you achieve that?
It's about listening a lot. It's about listening to learn instead of listening to respond with something.
Sometimes it's about trying not to solve problems immediately, but understand that I guiding the person asking questions and how will you solve the problem that tells me a lot about you as a person and it helps me understand how we can help you from the future.

[20:10] I really, really like that idea of how would you solve this problem instead of trying to leap into rescue?
And what I found is that Tetsuya Toyoda's five whys, going back to the why that we've talked about, is really powerful.
And from experience, you know, when it's been done to me, after that third why, it's like, just because, okay? Leave me alone.
But it's that fourth and that fifth why that really provide that powerful answer.
So to create that space for our team members to be comfortable sharing with us the responses as we go deeper into the pain funnel or through the five whys is really, really powerful.
Now, we've been talking like we are running the team and we're rolling out the change and things like that.
Sometimes as leaders, we get brought into a team and that team might have gone through a couple of bad pilots or, you know, changes that didn't go so well.
So for the leaders listening, what would you advise them if they're in a situation where they were brought in after to kind of clean up the mess, how do they build that rapport and how do they build that trust with their team so when they do roll out another change, they can successfully do it?
Because the previous manager might have understood their motivations and they still didn't do a successful change. That's a very good question.

[21:27] Once again, I'm going to give a similar answer to before. I think it starts with listening.
Listening and learning about what that scar tissue looks like.
Everybody comes with some sort of scar tissue. It can be anything.
It can be a previous experience. It can be a previous company I worked with.
But you're coming with your package of experience.
You're bringing that experience into the way you operate and into the way you react to anything that is happening today.
Part of the job of the manager is to.

[21:55] Learn how to get to the essence of that package and understanding how that package, how that experience is influencing the way the team is operating.

Team Dynamic and Change

[22:04] You talked about a team that I think it's interesting because a team dynamic is a little bit different than an individual rep dynamic.
And I think we need to look at that differently.

[22:16] As a manager, initially, you probably want to connect one-on-one with your team.
You want to make sure that you will get to that why, to that motivation individually.
Individually getting to know your team as a whole is a little bit of a different game a team will get to certain relationship dynamics that make it unique and i think there is a way of getting to a why of a team that is a separate entity than the why of the individuals within your team and it's a combination of how these different people are interacting within each other as a manager you can also influence what that looks like by scaling your values as a manager how do do you make sure that you are communicating and you are influencing with that? Why would that essence of the team also looks like?
So I guess I don't know if I answered your question, but I think I will definitely start with the listening and the learning, the individual relationship, and then translating that into how did that move into the team dynamic itself?
After you have learned, I'm a big, big proponent of you have to listen for double the time that you are speaking or acting or doing anything because, and that is very true in in sales, it's true in any other relationship.
It's true as a leader, it's true in everything you do.
The more you listen, the more you can actually gather information and it's gonna help you decide what is the most effective way of not only communicating change, but implementing change. What's the right timeline?
What's the right, what support does the team actually need to go through change in a positive way?

[23:42] I love that. And yes, I expected it was going to be very similar to the first conversation that we were having.

Building Trust After Failed Changes

[23:47] And I love this extra layer of, you know, looking at the team dynamic as well, because, you know, it's kind of like when you have a sport team and they get a new manager, but the team already has this culture and it overwhelms the manager as much as the manager want to have good intentions.
And so not only considering the individuals on our team, the overall team dynamic is really, really powerful.
So I'm very grateful that you shared that with our sales leaders who are listening around the world today.
Roberta, I have loved our conversations both today and previously, and we could probably talk all afternoon about change management.

[24:21] But we also have a lot of things on our plates right now. So I got a few other questions to wrap up with you today.
So the first one being, if you could go back and coach younger Roberta, go back as far as you like.
And say, hey, younger Roberta, in the future, you'll be director of sales at Dropbox, you'll have this great career. You're also going to have a lot of scar tissue and some bumps and bruises.
What would you coach younger Roberta to say or do differently to get to the same place, but with less scar tissue and fewer bumps and bruises?
I will probably tell my younger self to care more about the relationship than I did about the numbers and results and all of that.
And there is a part of this that is about, I do think relationships are more important than numbers and results there is also a selfish aspect to that that is relationships are what really brought me personally to success eventually and I couldn't have done without and when I started my career I thought I could put all of my input all of my work doing all it by myself and being successful at what I did and I didn't realize that my what actually eventually made me successful was the mentors that I got along the way the people that stopped a moment and helped me out.
So really caring about those interactions, valuing those interactions a lot more since the very beginning, I will give myself that advice.

[25:42] And maybe a little bit later in my career as well, vice versa, be intentional about supporting people you have around.
There are always people that are joining the workforce, that are joining the team, that are junior.
It's a gift to be able to support and build that network and provide value.
And I think we all work in sales and it's a difficult job.
It's a challenging environment.
And the support that you receive from your peers, from your team, from your cross-functional stakeholders, it would make everybody successful at it.

[26:15] What great advice and really resonates with me as well, because I have been very numbers focused and learning the power of, you know, the standing on the shoulders of giants, so to speak, is really, really powerful.

Recommended Books for Development

[26:26] So, Roberta, in your career, what have you read, listened to, watched, whether it was recently or in the past that you would encourage the sales leaders listening to go check out for their own personal and professional development?
So I'm a big book reader. So that's the way I learn. I think everybody has either a visual memory, so you read a lot of books, or an auditive memory, so you listen to podcasts. And I think both ways are very effective.
Books were for me. Radical Candor, I already brought it up, was the very first book I read as a manager.
It was very impactful in the way I think about leadership in general.
In terms of sales, a book that was impactful for me when I started was Let's Get Real or Let's Not Play.

[27:09] Lots of good sales advice in there. And then one more book that I actually want to say, it's not related to sales, not related to leadership.
It's called The Deep D.I.P. And it talks about the situations in life where you are going down a hall.
And does it make sense to keep going until you are out of the hall and you're getting to something better?
Or should you stop and move to something else?
And it was really good for me to get a different perspective in times when I thought I was like going down a hall and it didn't make sense.
Because I did eventually go out in a higher place and it was really, really good. Very short, small book.

[27:47] Very cool. We'll put links to all those in the show notes. Thank you for sharing those with our audience today. So last question for you. You have given us great ideas and insights already.
What do you have as a closing thought or a final bit of wisdom, maybe something to plug? The floor is yours.
I don't have a plug, but to go back to my advice to my younger self of building connections, connect with me on LinkedIn. I am...

[28:10] Planning to be more intentional about building those connections with my network, with the industry. I've learned the power of learning from others.
So please reach out. I'm always happy to chat about all things sales, change.
Yeah, that's it. Very cool. Well, Roberta, it has been an absolute pleasure to have you as a guest on Full Funnel Freedom. Thank you for being here today. Thank you.

Key Takeaways on Change Management

[28:33] Sales leaders, I absolutely loved visiting with Roberta today to talk about change. Of course, I have a book, Change the Sandler Way, that talks all about change.
And some of the big takeaways from Roberta's talk today really resonated with me, you know, specifically that idea of we have those change champions.
I call them, you know, angels, agnostics, and atheists in Change the Sandler Way, which is the angels are your change champions. They're the ones who are right on board.
The agnostics are the ones who are like, eh, we're going to kind of see which way the wind blows. and the atheists are the ones who are like, you know what?
I don't care if you're changing the coffee in the break room or our Zoom backgrounds, I'm against it.
And so really in empowering our change champions to get on board, show success, which is gonna bring that second group up and help the third group understand like, hey, this is the way things are going.
So if you don't wanna play, that's okay.
There's not a place for you in this organization anymore. more we still love you and you're no longer a good fit to be part of this organization the other big takeaway that i i really appreciated roberta bringing up is this idea of pilots and hypotheses and not getting stuck in oh i hope i get this result it's a hypothesis it's i think if i do this pilot i'm going to get these results and then if i do get those results i will then do this.

[29:57] Sometimes those experiments don't work the way we want and we get results that are like, oh, maybe I need to reposition or re-vector and we need to be open to that feedback as opposed to getting locked in on one solution where the pilot is basically yada yada in a way, the fact that we're going to implement something.
A true pilot is something where we're literally open to whatever the data comes back and shows us as a priority.
And lastly, this idea of understanding your individual team members why and the overall team's why and their culture.
Because if you're coming into a new team as a leader, you can unintentionally get blown away by the team's established culture, especially if there's some scar tissue from previous bad change implementations.
I'm really curious to hear about your big takeaways from today's episode on social media.
Thanks for listening. Until we connect on the next episode, go create full funnel freedom.
Thanks for listening to today's episode of the Full Funnel Freedom podcast.
You can continue to support us by leaving us a review and a rating, sharing this episode with a couple of sales leaders in your network who you care about.
I'd love to connect with you. I'm easy to find, Hamish Knox on LinkedIn.
Also, if you'd like a free 15-minute call with me, go to www.hamish.sandler.com forward slash howtosandler. Until we connect on the next episode, go create full funnel freedom.

[31:27] Music.