The movement for “walkable cities” in America has been gaining momentum on Twitter lately. What started as a niche “trad” take is starting to pop up in feeds across political and cultural lines.

So, if we all love walking so much, why are there so few walkable cities in this country? The answer is simple: we’ve invested decades of time, money, and effort into architecting our country around a different mode of transportation: the car. 

How would you transform the average American exurb into a charming, European-inspired hamlet? You would have to re-route roads, eliminate parking and downsize homes. Nothing short of blowing up the status quo and starting from scratch would deliver the desired result in a reasonable amount of time.

This tension between what we say we want and what we’ve got brings the challenges of change management to life. Like cities, business organizations are large, complex systems with their own architectural baggage. And at some point in your career, you’re going to run headfirst into your own “walkable cities” problem: you’ll need to change something about your employer’s “status quo” to do your job well.

In this situation, you have two options: influence the decision-makers, or move on to an environment that suits you more. There is a lot of MBA-style literature out there about “change management”. But this literature tells you what to do in some perfect, idealized organization–an organization that does not exist.

On the other hand, I have real-life experience guiding legacy retail brands into a future where traffic is no longer guaranteed. In some cases, I’ve been successful. In other cases, not so much. From this experience in very real organizations, I’m going to give you a tactical guide to change management. 

Step 0: Stop Hitting Yourself

Harsh truth time: the reason that people, or companies, remain “stuck” is not due to a lack of information. We all know how to eat healthy and save money, yet there are very few of us walking around with six-pack abs and perfect credit. Curious.

Some blockers are systemic (income inequality, microplastics in the water supply), and some blockers are things that we impose on ourselves (ordering a $10 sugary Starbucks drink every day). 

But in either case, when we are taking up the mantle of change, we’re also signing up to wage a battle against human nature itself. And when the odds are not in your favor, sometimes your best course of action is retreat.

Before you accept a new role or a new client, you need to understand how that employer/client defines success. You need at least a rough outline of how you’re going to achieve that success. And you need to determine if you’ll have the tools and resources available to carry out your plan. If you’re set up to fail from the start, then don’t start.

Of course, it’s impossible to do perfect diligence 100% of the time because people lie and situations change. You may have no other choice but to influence change within your organization or walk. So when should you try, and when should you walk?

I’ll give you one simple rule of thumb here: change doesn’t happen in a bull market. When things are going well, why would anyone change? “If it ain’t broke, don’t fix it” is a cliche for a reason.

I’m not saying that this is the way things should be. But in order to make change happen, you need to get people to acknowledge that there is something wrong with the status quo. And that something needs to feel meaningful to the people you’re trying to influence.

Good news for all potential change agents: it looks like we’re headed into a recession. So read on to learn from my mistakes so you can steward change effectively.

Step 1: Go Deep With Your Stakeholders

Your stakeholders are all the people who will potentially be impacted by the change you’re proposing. They’re also the people who have the power to block you or sabotage you.

There are two types of stakeholders: people whose reputation may be impacted by change (typically your superiors), and people whose work will be impacted by change (typically people you manage, peers, or other individual contributors).

Let’s get one thing out of the way: none of your stakeholders care about making your job more efficient or helping you achieve your KPIs. You have to kill your ego completely to be successful here. 

If you’re lucky, some of your stakeholders may care about making the company or your team more effective. But in the average organization, your superiors are focused on drumming up a list of digestible talking points that will look good to their superiors. 

And your own team, or others who execute, are typically change-averse because change means more work. Even if a new process makes their job faster, they will have to take time to step back and learn the new process. 

You also have to look out for knowledge hoarders within your stakeholder pool. These are people who cultivate complexity in an attempt to bolster job security: “Without me, this process will fall apart!” These folks will be particularly threatened by any attempts to streamline a process or adopt a new set of metrics or tools.

To succeed in making change, you’ll need to pitch your plan to all of your stakeholders, appealing to what matters to them. You’ll never win everyone over. At a bare minimum, you’ll need to get buy-in from the person or people who own the budget and enough executors to carry out the plan. The larger the organization, the more difficult this is.

Step 2: Provide A Different Way Of Understanding The Problem

It’s nearly impossible to make change happen when things are going well. But that doesn’t mean change is a cakewalk when things are going poorly. 

In an emergency situation, everyone regresses to the level of their training. And in eCom, it’s often that training that caused the emergency to occur in the first place.

When the business isn’t performing, executives will retreat to their corners and double down on their talking points. If Bob made his name at Starbucks building out the loyalty program, then Loyalty is the answer. If Sally grew Warby Parker with Facebook ads, then Ads are the answer.

The only way to break through this is to reframe the problem in terms that are completely tactic-agnostic, and ideally in a way that illuminates a net-new source of the problem.

One example that has occurred frequently in my eCommerce career: reframing growth issues in terms of new and returning customers instead of last-click channel performance. This helps unify channel-focused teams around a few metrics, and no single channel is “the problem”.

Reframing the problem often requires access to raw data and the application of unique analytical frameworks. Warning to all potential change agents: in a hyper-political organization, you will not be given access to data until you prove your loyalty to the party line. If you find yourself in a situation like this, get out as soon as possible.

Step 3: Quantify The Upside And Illuminate The Downside

At this stage, you know who you need to influence to get the ball rolling. You’ve also built credibility by helping your stakeholders understand the problem in a new light. This is the moment when you can introduce your solution to the person(s) who will sign the checks and the contracts.

The best way to do this is to put a business case together. If you’re looking to bring in a vendor or agency, this means evaluating at least three to five potential solutions and putting together an estimate of impact for each option. If you’re looking to change an internal process, you can propose one to three potential solutions, including your own.

This business case should make it clear that your proposed path forward is one of the better ones. However, you want your proposal to appear completely neutral–you’d be happy with any proposed solution, as long as it solves the problem.

If your organization is hyper-political, or if you have a weak or non-existent track record with your decision maker(s), you don’t even want to make a recommendation. Let them own the decision. But don’t include anything in the business case that you’d regret having to execute.

In addition to the business case, you want to develop a strong narrative about the cost of doing nothing. Inertia is always the easiest path forward. But if you’re standing on a burning platform, you have to jump off…or die.

Step 4: Propose A Pilot Or Test To Validate Your Idea

You want to position yourself to under-promise and over-deliver. Do not take anything a vendor says at face value. No one delivers ~25x ROI~ consistently to every client. And if you come in below your projections, your stakeholders will be out for blood.

A great way to do this? Propose a pilot or test to validate your idea. If you’re working with a vendor, propose a one to three month trial period where feasible. If you’re trying to implement a new process, find a subset of your team or a subset of tasks where you can do a trial run.

If the pilot is successful, you’ll get a ton of enthusiastic buy-in from the decision-makers/check signers. If the pilot isn’t as successful as you anticipated, you just saved yourself a huge headache. In a healthy organization, you’ll get points for trying. In a hyper-political organization, you can fail like this once or twice before you discredit yourself completely.

Step 5: Neutralize Peripheral Threats

Winning over your superiors/the check signers is often a numbers game. If you can distill your project into three bullet points that will look impressive on a slide deck or in an annual review, you can often win these folks over…if they trust you to execute.

But realizing those three bullets often requires cooperation from other team members who will actually “do the work”. These team members will have a myriad of other motivations that range from complacency to job security to “preserving the brand”.

You are unlikely to win over 100% of these stakeholders. If your company is small enough that you can own 100% of the project execution, you may not have to. But if you work for a larger organization, you’ll need to win over a few key people who will help make your vision a reality. And you need to neutralize anyone who might actively sabotage your plan.

Go into this process assuming that everyone has pure intentions unless you have proof to the contrary. Introduce your change proposal to each person or group, focusing on the ways it will benefit them. Do live walkthroughs and let teams sample the new processes or tools where feasible.

This process will reveal one or two potential champions–coworkers who are really on board with your idea. Get them actively involved in the project (to the extent they are comfortable doing so) and supply them with talking points they can use to raise their own profile within the company. 

This process will also reveal one or two active saboteurs. If these people have a tight relationship with your superiors/check signers, you have a few options. You can try to address their concerns, you can keep them on a “need to know” basis, or you can attempt to discredit them. All of these options are risky.

Step 6: Develop An Airtight Operational Plan & Execute Flawlessly

Your change won’t stick unless you put your money where your mouth is and back up your business case with real results. To succeed here you need to understand all the downstream impacts of your new software or process. 

An all too common nightmare scenario: you’re one week into a launch. Everything seems to be going smoothly, and you’re focused on optimizing program performance to hit the number in your business case. 

Then, suddenly, a call from finance/the warehouse/customer service/etc. Your launch created a huge issue that took a week to catch. It will require 40 hours of manual reconciliation–from you–while you also work to figure out why it happened in the first place. You are completely derailed, and this is all that anyone will remember about your “change”.

Do whatever is necessary to avoid this scenario. That often means digging deep into the legacy tech you’ll be integrating with, and developing a deeper understanding than the teams who manage it. It can also mean sitting with other team members to learn exactly how they do their jobs, and how your proposal might change their workflow. It’s time-consuming and tedious, but absolutely necessary.

Then, you put things into motion, and (hopefully) you exceed your goals. You’ve done it. You have made change. I hope you’re happy!

Caveats To Change

Caveat #1: There are a lot of business turnaround case studies written by and about CEOs, but very few books, podcasts, or blog posts about a Director of XYZ who transformed a dying business into a growth story. The scope of change you’re able to achieve is often capped by your level of seniority. The larger the organization, the more this is true.

Caveat #2: There are two types of issues: organizational issues and macro issues. Department stores like Macy's are struggling because consumer behavior evolved beyond their business model. Bringing in a new advertising agency or saving money on fulfillment costs are not going to change that. You can work towards organizational change in a negative macro environment, but you might find it unfulfilling.

Caveat #3: Even if you successfully implement change, some of your stakeholders may choose to walk away. Sometimes those who choose to walk away will be people you considered your closest allies. Successful change projects are great resume bullet points. If you publicize your change, competitors will poach your most effective lieutenants.

Caveat #4: The process will always take longer than you anticipate, and the results will never precisely match your vision. No one is going to hail you as “the changemaker”; if you succeed, they’re going to claim ownership for themselves. You have to take your ego out of the equation in every way. Change is actually much more satisfying for consensus builders than it is for trailblazers. If you want to blaze trails, start your own company.

Caveat #5: The above-average organization has processes in place to guide gradual, strategic evolution, so that disruptive change is almost never necessary. The average organization fights change but allows itself to be dragged along when the business hangs in the balance. The hyper-political organization has shadow processes in place to eliminate change agents before they know what hit them. Proceed with caution. 

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