The timeline of Salesforce announcements has felt ominous, surprising and doom-worthy to be sure:

  • November 30: Bret Taylor, Salesforce Co-CEO, announces he is stepping down effective January 2023
  • December 1: Mark Nelson, CEO of Salesforce's Tableau, departed the company
  • December 1: Steven Tamm, CTO of Salesforce, departed the company
  • December 5: Stewart Butterfield, founder and CEO of Slack, announced his departure
  • December 5: Tamar Yehoshua, CPO at Slack, announces her departure
  • December 5: Jonathan Prince, SVP Marketing, Brand and Communications at Slack, announces his departure

In the wake of the Taylor announcement I mused that someone really needed to go give Marc Benioff a hug as I imagined him standing alone, once again, in Salesforce park with nobody to play with. And to some degree, I still feel that. Benioff has seen a LOT of departure in the past couple of weeks, and not just from Salesforce as Keith Grossman, President of Time Magazine, who notoriously dragged the pub into the web3-powered metaverse announced his departure days before the Taylor bombshell. 

It is hard to turn in any direction and NOT see a report about these departures..along with others reported earlier in the fall like Gavin Patterson's intended departure in January 2023. Some journalists and even some of my analyst peers have taken to social to announce the fatal blow these departures will have on the tech giant. Some comments, it should be mentioned, are down right giddy with anticipation for the pain. Some of these headlines are click bait. Some of the comments are to be cantankerous or persnickity. Some prove that Business Insider LOVES a leaked org chart. Some raise really interesting questions from why to now what.

It is exceedingly easy, especially in the immediate aftermath of big announcements, to imagine a world where NO organization could EVER be the same after someone departs. Slack will never again be Butterfield's Slack. Taylor's shoes are too big...too mission be filled. 

Here's the thing...and I say this with ALL due respect to both Butterfield and Taylor...everyone is replaceable. Slack will never again be Butterfield's Slack...and that's OK. The question here isn't CAN they be replaced but how well does Salesforce understand Salesforce to correctly map the succession opportunity before them. The opportunity here is to replace those leaders departing with new thinkers that understand that the job isn't to FILL shoes but to cobble a whole new pair that are distinctly theirs. 

The Fallacy of Shoe Filling

As I sit here writing I've been struggling to think of a successful executive who was able to step into a highly visible role by pretending to BE the person they replaced. Tim Cook didn't pretend to be Steve Jobs. Instead, he respectfully and carefully picked up Job's insanely large shoes-to-fill, placed them in a spot of reverence, and then started cobbling his own shoes. When Tim Cook chooses to retire, he too will leave massive shoes to be filled. But they won't be Steve Jobs' kicks.

Let's take the example of Butterfield's departure. In an analyst fireside chat held today (12/6) Butterfield shared that this decision process dates back months. We now know that Lidiane Jones, the current GM of Experience Cloud, Commerce and Marketing Cloud with Salesforce, has been tapped for the role of Slack CEO. This is an executive that has seen Commerce and Marketing Clouds through a significant platform and integration transformation. She's no slouch. She understands the vision, the product, the customer and Salesforce well.

In an age when every corner of tech's opinion-verse touts the criticality of digital ecosystems that can combine customer experience (CX) with employee experience (EX), who better than a CX leader coming to advance the vision for a Digital HQ that includes Slack's capacity to address EX in the service of CX? 

Butterfield's shoes are Slacktastically big...but this isn't a question if Jones can fill Butterfield's shoes. Those are his and his alone. The question SHOULD be what shoes will she make? Will they be distinctly molded to more fully embrace this combined CX + EX vision for Slack? Will they carry the water for a DigitalHQ message or will they evolve that message into its next iteration? Time will tell how well this succession model unfolds. And if I am being honest...I'm far more interested in who is eyeing HER shoes in the CX solutions than concerned for how well she will do in her role with Slack!

Stop Asking About the Plan...Ask About the Strategy

But this does bring us to the issue of succession planning. Succession planning is vastly different than "filling an open position" which is a process. Succession planning is a strategy that culminates in the process of filling the vacancy that is initiated when a leader leaves. Having been part of succession strategy sessions, I've noticed that much like developing customer experience strategies, going on gut, mirroring past actions or guessing-as-strategy typically ends in failure. Guessing is not a strategy 

So where can succession planning avoid guessing? Often times the strategy starts by clearly articulating the top business challenges that the organization could face over the near term and long term, with a focus on those long term "5-years from now" issues and throwing in some of those wild curve ball challenges like a global pandemic just for kicks. Skills, both hard and soft, are also outlined and cataloged, typically based on the positive skills and attributes of the departing leader. In scenarios where cultural change is required, noting any missing skills or skills and attributes to avoid is a wise exercise. 

As the strategy is outlined, there also comes a time to document the teams, leaders and positions that will be critical to ensure near term business continuity and long term success. This is typically where individual names start to bubble up to the surface...individuals who invariably end up placed somewhere in the theoretical line of succession. They may have many of the attributes desired in the next leader. They may be at the helm of mission critical departments. They may be influential partners in the business eco-system. They may be a fan favorite with the outgoing boss. 

Regardless of why they bubble...names start to bubble. And this, sadly, is where some of the guessing begins. We guess that this person will be successful because the former-CEO liked them, they worked well with the board, they hit their goals, the team loves them...all amazingly positive bullet points for a CV...but the guess is still there. 

Networks for Change

While doing research for a report published earlier this year titled "People-Powered Revenue Intelligence" (link gated) I had the opportunity to interview the team at Introhive, the customer intelligence solution, about their work with network analysis among teams and internal organization stakeholders. While talking about change-centric programs like diversity or leadership advancements, the team noted that the data to understand WHY leaders are successful is right under our noses: the data in emails, chats and business communications that can unlock the secrets to what and who is part of a successful network. The question can then shift from "why don't we have more women in leadership roles" to "what network, connections and work actions does this successful woman leader in our organization do that others can replicate and that the organization can support, facilitate and encourage?"

By flipping the script from guessing to knowing about success, traits or attributes, people-powered network intelligence can start to architect the network infrastructure that can be built around individuals with the intent to realize and replicate change. So, through the lens of succession planning, knowing what network a successful outgoing CEO had becomes critical data to inform what network the incoming CEO will need to enact their vision and plans. 

What does this mean for Salesforce? Perhaps nothing at the moment. But as we have seen in the Butterfield to Jones baton handoff, when succession strategy is executed, it can set up the incoming leader for success even in the face of the crowd shouting about imminent demise. Yes, curveballs can appear out of nowhere and for Jones, Slack and Salesforce that curveball was named Bret. Time will tell if succession talks had tackled the scenario of 'what if Taylor departs' or if those Taylor-related conversations were only specific to 'what if Benioff departs' discussions. 

For right now, the reality is that as much as Taylor et al. will be missed...Salesforce will soldier on with new leaders stepping into the footprints of big shoes. The real question to be answered will be if these new leaders will spend their days trying to fill old shoes or if they are ready to cobble their own way forward.