Strategy, execution, & communication challenges in management - Barry O'Reilly

Strategy, execution, & communication challenges in management - Barry O'Reilly

As part of our new podcast series, Just3Things CEO Ed Janvrin sat down with entrepreneur, business advisor, and author Barry O'Reilly to discuss all things management, execution, and business strategy. Barry and Ed covered the main changes they've seen in the past 5-10 years, as well as the challenges facing managers today.

The blog is in interview format, with Ed posing the questions, and Barry giving his expert insight!


I wanted to start by exploring the changes seen over the last 5-10 years in the way that managers and executive teams drive business execution. How have you seen things change?

A couple of the things that are really standing out to me is this notion of people really tying into the purpose of the businesses, if they’re unable to tie their effort to outcomes that are affecting the purpose of the business they're part of, it's very easy for people to walk away from those companies very quickly.

In many ways, the great resignation was less about people not wanting to work, but more that it was because they didn't feel connected to the purpose of the companies that they've joined. So I think those things didn't go away, and people have just gone to find places to work that they can really dial into the purpose, and every day connect the effort they're putting in to the outcomes that are achieving that purpose. So I think that's one thing that's really stood out to me, especially the last two years during the pandemic and as we sort of start to come out of that, it's just a shining light. 

Another one that really struck me, and this came up a lot when we were doing the executive roundtables at Slack over the last three years, is that people care more about when they work, not where they work. And this was a big aha moment because so much of the debate has been about are you remote, are you hybrid, or are you some other version of that? But actually, what really matters more is when people are working today. 

And this, I think, has led to the rise of asynchronous communication. One of the things that was a standout for me, was that at Slack, all of the big old town hall communication meetings that used to take hours just disappeared, and there were much more frequent shorter updates, almost akin to social media, like five-minute updates every other day about what mattered for the business, rather than these big production meetings

I often think that Slack is more like a game. It's more like a social media platform. Right? Where people are sharing updates. That's what they're sharing, bite-size digestible content that people could list out. This is one of the other things that stood out to me, as they could watch these things when it mattered to them. There wasn't a case of suddenly we have to do the big all hands meeting on Wednesdays at noon, Pacific time, meaning that some have to stay up late etc. This is probably one of the great things I've learned again through your question of the differences and developments in business execution. 

I often think that Slack is more like a game. It's more like a social media platform. Right? Where people are sharing updates. That's what they're sharing, bite size digestible content that people could list out.

Really great execution is about great documentation. Whether that is one-pagers or press releases, like great and simple explanations about what your product is about and what you're trying to do. Bite-size but really clear communications for readers, five minutes, three minute little videos to really keep reaffirming the context about what success is and why it matters. But choices the business makes in these small digestible formats. 

Great teams can then come to meetings to discuss the decision, not to discuss what the meeting is about. Give me the context, what's the artifact? Then let's debate it and close. That takes up too much time now, as I'm constantly seeing great teams sending out the content in advance, setting the scene for the decisions that need to be made. We're also experiencing this at Nobody Studios, we’re a globally distributed team, with people in London, Italy, America, Africa, Asia, Australia, Philippines. So times when people are all on the same call are so valuable, that every moment has to be used to make decisions so people can keep moving fast. Not an hour where people wait 25 minutes to figure out what the hell is this meeting about what decisions need to be made? 

Really great execution is about great documentation. Whether that is one pagers or press releases, like great and simple explanations about what your product is about and what you're trying to do. Bite size but really clear communications for readers, five minutes, three minute little videos to really keep reaffirming the context about what success is and why it matters

So the change in the way people work and this realisation of the when rather than the where, and then tie with that the changes in communication. I guess it's forms of communication that are available to us, which will change the way that you can execute your business. 

Social media has trained us to want high-impact bite-sized content all the time.


What would you say are the major challenges that are facing business managers to actually execute against their set strategy in businesses today?

For me, I think the hard part always is moving information around your organisation, and also making sure it’s the right information at the right time, helping people but not overwhelming them. Information that doesn't distract them from the task at hand, but does make them feel aware of just enough of what's coming around the next corner and what's over the next hill, rather than being overwhelmed with “you need to get this done today and tomorrow”. I think it's one of these skills about timing and the type of information you're communicating has never mattered more. It just keeps helping people feel connected to the direction that the company's going and the challenges the opportunities etc that are offered. 

For me, I think the hard part always is moving information around your organisation, and also making sure it’s the right information at the right time, helping people but not overwhelming them.

If I want to find out what's going on, where are we going? Oh, something interesting happened? We signed a new deal? A new partnership deal, or we had a great sales month, or we're struggling to find talent in a specific area etc. This helps employees and colleagues discover how they can tie their work to business goals, and how the I'm doing on my desk is somehow connected to this bigger place that we're trying to go, which is a very powerful way to keep people aligned, engaged, all that good things that we're looking for and great companies.


With a lack of communication, some will think there’s more going on than there actually is. With that said, how does a good organisation deal with that challenge?

Transparency is this idea of it's a double-edged sword. Right, like you don't want to overwhelm people with demands from every single management meeting, but it’ll take them 40 minutes to read meeting notes, taking a percentage of their working week away from them, just to read the meat of a management meeting, which most of the time would put people to sleep. 

It’s just about explaining the why. “Why is the CEO traveling for the next few weeks? Oh, because they're trying to sign partnership deals.”, “Why are we changing our investment strategy on the kind of new products we want to build? Like, why are we doing that?” 

I think that's why bite-sized bits of content help, as they just relieve a little bit of that pressure and that opaqueness whereby it can feel like you're not connected to what's going on. People don’t have to know everything, or even want to, they just want to know enough. It's one of these things that I think is such an innate skill of great leaders, but it's never taught anywhere.

Yeah, I've never gone to a school that teaches you how to know when to communicate the right information at the right time. It's a trial and error process. And believe me, I've made plenty of mistakes as leaders in companies where I felt like I was being transparent and told people probably too much information, but actually caused more ambiguity because I was overloading people with things that matter to them. You know, and it's a hard one right? And I think you can only really learn it by putting yourself out there making a few mistakes and then finding what the right level is. 

I've never gone to a school that teaches you how to know when to communicate the right information at the right time. It's a trial and error process. And believe me, I've made plenty of mistakes as leaders in companies where I felt like I was being transparent and told people probably too much information

What can people cope with? Like some people can cope knowing stressors in a startup, you know, you've got two weeks of runway left to close the business. Some people can cope with that, but a lot of people can't. Right. It would distract them from their job. So yeah, you just have to meet people where they're at and help people be successful and be authentic.


Barry O'Reilly Bio

Barry O’Reilly is an entrepreneur, business advisor and author who has pioneered the intersection of business model innovation, product development, organisational design, and culture transformation.

Barry is the co-founder of Nobody Studios, a crowd-infused, high-velocity venture studio with the mission to create 100 compelling companies over the next 5 years.

Barry is author of two international bestsellers, Unlearn: Let Go of Past Success to Achieve Extraordinary Results, and Lean Enterprise: How High Performance Organisations Innovate at Scale—part of the Eric Ries series, and a HBR must read for CEOs and business leaders. He writes for The Economist, and is faculty at Singularity University.


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