You want to make progress. You know that you are an innovator for your organization. You simply want people to listen to you, yet your voice and any challenge you put forth to do the right thing seems to go unheard or unrecognized. You need to ask yourself “why?” I get it, it can be very frustrating when you probably have the answer to a problem and are trying to prevent your company from settling for the status quo. So how can you get your voice heard? Let me ask you this: “Do you think you have been challenging appropriately?” Now “appropriately” sounds like I am just talking about being “nice”. It is actually much, much, more than that, which is why challenging appropriately is in fact, a challenge. For some of us, the answer is intelligent disobedience, but for some of us, it is learning how to challenge appropriately.

There are many barriers to challenging successfully. I often joke that the root cause of these barriers is that people suck! Now I mean this in the nicest possible way, I love people – I really do! I am first and foremost a people person, however, I know that people want what they want, when they want it. People are different: personalities, needs, desires, goals, experiences, and more. People are just hard to figure out. What we think is obvious and should be acknowledged, another thinks is ludicrous and walks away. Add to it the complexity of communication and you run into many more barriers like: wrong place, wrong time, wrong person, wrong facts, wrong approach, not enough alternatives, budget, resources, personal pride, personal agendas, positional authority, your dog ate your homework… well, there is simply a lot that can get in your way.

What does it mean to challenge appropriately? I think there are many things that make up the definition. My personal definition is:

“An individual or group, who works with other individuals, groups or organizational structures in a collaborative fashion, challenging the status quo to achieve a common purpose or goal for the greater good of the people, project, or the organization.”

This is all well and good as a definition, but it still does not tell us how to challenge properly. It would be great if we could first all agree that we should have the ability and right to challenge as part of collaboration to ensure we meet the goals appropriately, but all of those “barriers” come creeping in quickly. So what can you do?

There are 100’s of ideas that I am sure everyone has, so I hope that everyone chimes in with their favourite ways of increasing the chances of challenging successfully. Certainly there are some basic rules that we should all abide by when challenging - mutual respect, being nice, honest, positive, seeking to understand, critically thinking and not rushing to judge, open minded, and being flexible and adaptable.

Here are 6 tips that have helped me for over the years successfully challenge for the greater good.

1. Know thyself. It is advice I have given for years. As I have worked with people from all walks of life, I have found that those who are able to challenge appropriately are those that have a strong sense of who they are and what they want out of life. The better you know yourself, the better chance you have of dealing with other people because at the very least you have a strong center to work from. I know exactly what my strengths and weaknesses are, what type of person I am, what I want out of life. All of this gives me an opportunity to relate to people better. Think Myers-Briggs Type Indicator, Insights Discovery Personal Profile, or Strengths Finder 2.0 is beneath you? They have all been my best friends and valued tools for many years. I am happier now than I ever have been because of these tools and how they have helped me shape who I am. They have helped me know myself.
2. Know what motivates people. What is their WIIFM factor? WIIFM – what’s in it for me? It is hard to challenge successfully unless you know what is going on in the mind of the other individual and what is motivating them. It is often impossible to influence others without understanding their motivation. And that is the whole reason for challenging, right? You are trying to influence them to another way of thinking and doing. How do you do this? Perhaps just ask! Most people will tell you. Keep it simple like “Hey Jon, help me understand…” Notice I did not put the word “you” in that question. Don’t put anyone on the defensive with the “you” trigger. A natural, organic conversation will often yield how people feel about things – their WIIFM.
3. Know the facts. I’ll take some mastery of the facts with a side of options, please. A challenge without a mastery of the facts can be perceived as incompetence. If you talk to your boss about changing something, or complain about something that does not work, and you have not given them any options with sound facts for how it can be resolved, you will often be perceived as a whiner. Make sure you have more than just your gut feel for something. Yes, for most people, your gut is likely to be right, but many people will not proceed or agree based off a gut reaction or instinct. Details are needed. And if you do have the facts? Make sure you have a backup plan – options. Not everyone is going to respond to your first option. Always have a backup. Even if your goal is to show them the backup so that they realize the first option is the best way to go.
4. Time and location. If you challenge at the wrong time or in the wrong location you might as well have not tried at all. Understand the implications of the when and where. Once upon a time I tried to challenge something early in the morning. I am not a morning person. I am often incoherent until after 9 a.m. Okay, maybe 11 a.m. if I am honest. Although I had my facts, I was not articulating them well. Although never formally diagnosed, I sometimes speak my words backwards – a form of dyslexia. After making my case, people just stared at me and then continued in a conversation like I was not there. When I am focused and alert it does not happen. I also do not drink coffee, so good mornings for me are generally dependent on good sleep. I also once tried to challenge something in the office of a Senior VP. Well, let’s just say that I was not given the time of day as he paid attention to his computer and everything else in his office. I had the “when” right but not the “where”. Your strategy of when and where can make all the difference in your results.
5. Coalitions. I do not often challenge alone - I find strength in numbers. A coalition is a group of like-minded people that share your vision. People in your coalition may have strengths that you do not (of course you need to know what those are first). When I challenge, I am keenly aware that I do not always need to be the frontrunner for the challenge. I am okay if there is someone else better suited to do so. It is the end goal we need to get to and my ego is checked at the door.
6. Know how often to challenge. Challenge, and then challenge again! I often talk to people about how they challenge. The story usually goes something like “I brought it up to them that it was not going to work, I offered a solution and they just ignored me!” Well, that is not really a full challenge. That is an attempt. A challenge is something that often needs to be sustained or repeated. You must be willing to go back to the well if you believe in your cause. For most things I use the approach of: “Two toots and a salute!” This is the idea that you challenge once, and when no movement or resolution comes forth, challenge again in a different way through coalition members, other creative options, or new facts. Still no movement? Then it is time for “Yes, sir!” “Yes, ma’am!” You must be aware that pushing too hard can result in a CLM (career limiting move). Figure out both what the individual and organizational tolerance is for challenge so that you can adjust your strategy accordingly. There are definitely times I will challenge three or four times if the tolerance is there, especially when I have the facts and the support.

At the end of the day you want to help move your organization forward. You want people to listen to you. You want to do the right thing. I believe that when we challenge appropriately it helps to build relationships and foster better collaboration. Intelligent disobedience works too, but a balance between these two things is even better. So where have you had success with challenging appropriately? What is your strategy to remove the “challenge” from challenging?