20-Minute Leaders

"It used to be that decisions were made at the top and then those orders came down. But that's almost reversed"

Ilan Frank, VP of product at Slack speaks with Michael Matias about how to increase productivity and have fun while doing it

CTech 12:1931.12.20

From phone calls, to emails, to texts, society has become accustomed to instant and informal messaging, and Ilan Frank, VP of Product at Slack, is helping companies adapt to this new form of communication. Frank understands how important effective communication between employer and employee is, especially as more and more decisions are being made among teams rather than executives. After working at Slack for four years, Frank has also learned how valuable customer feedback is and encourages startups and established businesses alike to set up customer advisory boards where directors can meet with and talk to current users. A company cannot assume they know what their customers want, and Frank explains that all organizations should thoroughly listen to the concerns that their users present. Through this work, Frank has helped companies transition to an updated form of communication and in doing so has fostered a more connected and receptive environment for all. Frank sat down with Michael Matias, creator of the 20MinuteLeaders video podcast and told him about the fostering widespread change, one team at a time. 



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You have had 20 years of experience in this space in leadership positions, most recently now it’s Slack. One of the things we talked about, the unifying thing throughout the journey of yours, is the fact that you are passionate about collaborative software. Is that an accident or is that intentional?


I accidentally ended in enterprise software because my cousin was a venture capitalist back in the early days and he pointed me to a startup that he invested in that happened to be in enterprise space, and that was my initial journey in Silicon Valley back in 1997 and that’s what started enterprise software for me. But once I found the (enterprise) collaboration, I found a group with a passion and I have been pretty much there ever since!


As a veteran of the industry, what are the secrets you learned along the way? What would you tell young Ilan?


With regards to enterprise software, it’s really important to focus on the end users. That is something we did not know 20 years ago that maybe it’s more obvious now, but that’s something that’s critically important. I think what’s more relevant now is that enterprise software needs to be designed well. That the adoption metrics have to be taken into consideration, but we seem to have forgotten that enterprise software has to be something different from consumer. Enterprise software has a user and a chooser. It is important as the chooser that the person who makes the budget decisions is the person who makes the buying decisions. It’s important to consider them in project management just as much as the end user.


Why is that? Is it like a budget cycle where I go to the enterprise, I pitch the software to the director who has the authority to sign off $100,000 for software and the end users are his team players who are actually using the software for whatever they are doing?


Right, the dynamic is these days, the software is more bottom up rather than top down. Rather than the CIO taking the decision on software, it's being found by the ICs, the individual contributors that actually have the job. They want to be more productive at work. They are looking for tools that will make the work more productive. That’s why it’s important to focus on the end user, and lots of software companies like Slack are doing so. One of the things people don’t realize about Slack is that we focus equally on the top down. What is going to be important for the enterprise buyer, what are the tools that are going to help my employees transform themselves to be more productive and innovative?


So you are saying there has been a trend changing, that previously if you go to the CIO and you pitch your product, today you are going after the team players, and get them to love the product so they get it for their organization?


That’s right, it bubbles up to the CIO, he sees it, and as a software company, you want to sell to the CIO. This is when the CIO is going to look for different things. Their requirements are very very different from the end users. Beyond cost, they also have to look after compliance, security, administration, and performance. Those are the things that really matter to them.


Ilan your colleague may have data from millions of customers, but you are coming in with a handful of enterprise customers, how do you get data like NPS scores from those individuals who are buying the software, because your metric is their satisfaction. Usually you have to tell customers what they want, ask them what they need. Is that right?


I want to make sure that people who are starting enterprise companies understand that. Yes, that’s true, customers don’t necessarily know the solution. They will ask for something that sounds like a solution. What you need to do as a good PM is to get them to state the problem. Bring them back to the problem and give them a solution. A lot of the time people think the customers don’t know what they want. “I know what they want. I will go and build something without talking to them.” That is not the right strategy, and it will not work!


With enterprise software, you don’t have many data points, but you can certainly go and talk to people. That’s the first thing I will advise. Meet regularly with your top customers. Present them with the roadmap and get their feedback. We have special sessions to drill down on the areas to focus on in the future. We really want to get their input on the specifics. Lastly, make a session for them to talk to one another. So, the best part of the day is having them talk to us. Talk about the things that are working and things that are not working. We learn from them.


What happens when there is a clash between the roadmaps of Enterprise and Self-serve?


A lot of it is art more than science. On the enterprise side, it’s the revenue that’s impacted. Based on reports that show us where to invest in the big security or administrative features, and on the retail side, the metrics tell you where to invest. We have a lot of experiments that we run to see what proves to be better. Now enterprise to retail is a bit more difficult. For that, we have company priorities. We pitch internally, and it has to align with the company initiatives and the teams that align with those initiatives are the ones who get the resources.


Looking forward, we have a global pandemic which changed the world forever, our workforce has changed, I would love your take on where we are headed.


It is certain that we are not going to the ‘normal’ that we’ve grown accustomed to. However, the office is not a thing of the past; we will have offices again, but it will be slightly different. We have realized that people can be just as productive at home. The trend that we have seen is that responsibility for decision making is brought down the chart. It used to be that orders came down, but now the decisions are made in teams. Executives know what decisions are being made and that’s healthy for large organizations. That kind of reverse information flow is a new area that is going to be explored with tools like enterprise software.


Are we going towards real time collaboration, multiple integrations? Are we going to see better happiness levels because of that?


I think people can be both productive and happy. A lot of times they complement each other. I don’t think of happiness as only socializing at work. In any future company I may go to, I couldn’t imagine coming in the morning and opening an inbox of 100-200 emails; it just seems so counterproductive to have my information sorted in that manner. In Slack, I decide what’s important to me. It's backward to think of email in the future. You would see channel-based communication, like subscribing to the project and the topics I care about. Email is just organized chronologically; it just isn’t organized well. Slack is now organizing your work based on topics.


The email is too formal. Now with Superhuman or Slack, when my manager Slacks me, it feels like the same conversation, it makes me respond faster, more confidently. It makes everything more fun?


Yes, and more productive. I use emojis in conversation now. I use the eye emoji to show I am reading the message and then a green check box to show I have read it.


Can you describe yourself in three words?


Hardworking, Collaborative and Humble.



Michael Matias. Photo: Courtesy Michael Matias. Photo: Courtesy

Michael Matias, Forbes 30 Under 30, is the author of Age is Only an Int: Lessons I Learned as a Young Entrepreneur. He studies Artificial Intelligence at Stanford University, while working as a software engineer at Hippo Insurance and as a Senior Associate at J-Ventures. Matias previously served as an officer in the 8200 unit. 20MinuteLeaders is a tech entrepreneurship interview series featuring one-on-one interviews with fascinating founders, innovators and thought leaders sharing their journeys and experiences.


Contributing editors: Michael Matias, Amanda Katz