Gut check your digital leadership toolbox

Being a true digital leader requires more than a wardrobe change

Fintech leaders have disrupted more than just the role of technology in the advice industry. Every company leader wants to be with these new cool kids. I counted just three ties at a recent gathering of 80 companies. The talk is invigorating — all about innovation and breaking from the past. Go ahead and undo that second button on your shirt!

Alas, for most of the advice industry, the reality is more confining — and buttoned up. Most of the industry assets are owned by older people getting older using big firms with slothful legacy systems and prone to product sales. If “wealth management” were a restaurant, the industry skews more Cracker Barrel than Cipriani.

Energized by visiting one of perhaps 200 fintech gatherings or scrolling through LinkedIn posts by hip competitors in skinny jeans and high top sneakers, more than one leader has called on the company to be “reborn digital” and to “imagine” a frictionless future in which advisers are empowered by a client-centric headquarters team to delight their customers with a customized menu of savory solutions aligned perfectly with their next best action.

Defining the journey

Reality is more sobering. Like the new fitness enthusiast trying to transform her (or his) aging body, the advice industry leader is weighted down by the trans fats of legacy tech, anxious compliance and human resistance to change. The CRM is the ubiquitous rowing machine or Soloflex you bought years ago and is still mostly used only when you have to. Being “digital” sounds exciting but is more often a slogan in search of a business plan.

The authentic digital leader knows and models the transformation to more digital solutions by acknowledging the current reality and candidly defining the journey. Too often, the organization’s addiction to sales derails the plan like a frosted doughnut. But truly insightful leaders anticipate the distractions and move beyond the temptations by focusing the team on a single shared objective and rewarding the focus with jobs made easier.

Because leaders are always being watched carefully by their teams, they are gifted the opportunity of influence every day — many times a day. Modeling desired behaviors starts at the top and digital savvy is easy to see — or not. Where do you show up? Locked up in the corner office or moving among the team talking — and mostly listening? Are you on social, do you conduct meetings with boxes of printed PowerPoint or scroll an iPad? Do you reply to emails and texts, do you dress like your trying too hard?

The business stuff is where you make stick the forward vision. Has your team had the chance to inventory clearly and vocally the points of greatest pain in the organization that stand in the way of progress? Is that list understood for its impact on clients and advisers? How does the list compare to your tech investment prioritization and the alignment of your resources? One observation of mine is the proclivity of firms to depend too heavily on internal IT resources based on the competence of those people. The issue is seldom competence — it’s bandwidth and focus. If you have a few good people who can do anything, the challenge is to protect them from everything. Give them the time and space to complete a key project or get an initiative on solid ground. Even a SWAT team of stars needs time to take out the enemy.

Fear and desire

The enemies of the digital savvy leader are mostly human fears — and desires. The best leaders listen carefully and thoughtfully to employee concerns and do not try to inspire people past their apprehension. Likewise, folks who enjoy what they do can visualize a future where the company may not want or need them. These are genuine issues that prevent otherwise intelligent people from signing up for new future.

A lot of leaders will dismiss these words with confidence, their style and persistence will win over the team. Perhaps. But given the demands of true incorporation of digital capabilities, I’d want to save my passion for the inevitable bumps in the road ahead.

Gut check your digital leadership toolbox. You’ll need some basics.

Find the mold. The most common excuse for not doing anything new in a company is “it’s always been that way.” The next question needs to be “why,” followed quickly by “what would it take to get back to the beginning?” Much like repainting repeatedly only to see stains reappear means you have mold that must be removed. What is the real cause of the problem or the friction or the bad policy and be prepared to discover a more difficult challenge than you first thought. And keep going!

Use seeing-eye dogs. My team at Fidelity had me, the new guy, and mostly longtime company veterans hand selected for their loyalty to the firm. My role was to suggest what we might do to win and the team was assigned how to win at Fidelity. I once watched a business unit executive at another big firm run a search for a CAO with the initial screen that she didn’t want any “company people.” She wanted fresh thinking. Admirable but impractical. The greatest value of a seeing-eye dog is to keep you safe when a bad driver runs the red light. It’s not a “comfort” animal.

Recognize the first “wins” you get from digitization are the things you stop doing. In the Fidelity branch system, for example, we wanted the associates to engage more with clients. But they didn’t make real progress until we got them out of the business of taking checks, sending wires and filling out forms. Digital tools free up human capacity to do things only humans can do. Caution here — be sure you never forget the flip side of freeing up time for people. It is not the objective to eliminate them or make them work harder. Instead, the objective is to make jobs simpler and easier to do — and more rewarding. Don’t assume your team understands those objectives.

[Recommended video:​ How the client experience will be different in five years]

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Steve Gresham is a wealth management industry consultant and Whealthtech investor. He was formerly head of of the Fidelity Private Client Group. See more at thegreshamco.com