The train is leaving. We want you on it, but it is leaving…

Are you an entrepreneur or a younger individual poised to take over some leadership duties at your company?

If so, you may find it’s difficult at times to sell new initiatives, especially as it relates to Digital Marketing and Digital Transformation. Here are some tips to help you on your journey.

1 – Put yourself in the current leaders’ shoes … and show some respect
It’s probably an exciting time for you and probably a nerve-wracking time for older (wiser) generations. They’ve spent the past 20, 30, 40 etc. years building and protecting the company you work for and it was their blood, sweat and tears that has the company in it’s current (successful) spot. They have sentimental value about their brand, about the culture of the company, their history, etc… and they should! Above all else, they want to make sure their efforts have a lasting and positive effect. Handing the reins to young, (at times) untested newbies can be scary (and rightfully so!).

We will feel the same way someday about our efforts. If you can put in an effort to understand this, it will naturally show and it will go a long way with them inviting you to the table.

2 – Find the most progressive and open minded leader at the company
There is bound to be someone at the firm that is always open to new thoughts and ideas. Find this person. Take this person out to lunch and keep the conversation loose. Mention that over the next 6-12 months, the company needs to start exploring becoming more Digital. To do so, it should be done in a parallel path to what is tried and true. If the company currently likes hard mailers, directory listings and magazine advertisements, fine. Keep doing them, but also carve out some budget to explore a Digital Marketing Roadmap and some quick wins like a refreshed website, E-mail newsletters & nurture campaigns, SEM & PPC, Social etc.

I always say, it’s more important to get started then it is to be perfect with new initiatives (because it’s the hardest part). Once moving, you can use the momentum to keep building.

Having an Executive on board that knows the other Executives will naturally be able to get them on board with giving things a chance, whether it’s because of friendships, reputation, ownership, etc.

3 – Don’t be afraid to admit what’s not going well, but make sure the whole story is told
There are a lot of people out there that are not big picture thinkers, which is totally fine. Although, you need to be ready to both appease and disarm them. With Digital Marketing, there will likely be multiple mini projects in the beginning. In an ideal world, they will all go well. In the real world, it’s more likely that some will go really well, some will go okay and some will fail. The ones that fail are likely to be honed in on by certain people who want to shut everything down as a result.

Don’t overreact. In the words of my former boss, put yourself in a shit sandwhich. Start by talking about the state of the project, as a whole, reiterating how great it is that the company is moving with the times. Then admit the pieces that are not going well along with your plan to remedy them. Close out by also talking about the things that did go well. People will appreciate the honesty and good executives will see that the over-all initiative is important and moving forward.

If you just focus on the bad right away, that will take over the conversation and shut you down. Trust me…

4 – Don’t try to please everyone
Also remember that there is a limit to everything. It’s important to bring people along with you, but the naysayers can sap your energy and the project’s. At some point, you might have to just politely keep your head down and stay out of their way.

Focus on the good stuff you’re doing…and more importantly the people that are on board.

5 – Have Fun and make your intentions known
Probably the most important aspect. Have fun. Smile more. Joke around. In dealing with Digital Marketing, we’re not heart surgeons where the smallest mistake can be fatal. This project should be exciting and well known among the company. If done right, it builds culture, excites the community and gets your client new clients.

… and in doing so, don’t be secretive about it. Give regular updates, celebrate the quick wins, and update people on the failures (and their associated adjustments). At some point, you’ll realize you’re no longer in a Digital Transformation stage. Instead, you just work at a company that is now on the leading edge of all things Digital.


Coming full circle with the title, I always advise my clients to tell their Executive Teams that the train is leaving.

We want as many people on that train as possible. We will hold the train at the station for as long as possible. We will make the ride as comfortable as possible. However, that train is leaving and if you chose not to get on it, you’ll be left at the station.

Shameless plug. If you are in the midst of this or need help with your digital marketing, my team and I are well versed and at your service 🙂

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