Here’s the takeaway: if you’ve never had the Chick-fil-A milkshake, you’ve got to try it. And as you are enjoying that tasty treat, let it remind you of the power you have to challenge up. Existing paradigms can change, but it takes wisdom, patience, and the right strategy. You don’t need authority, but you will need influence. You don’t have to be the one in charge to shift the paradigm and challenge the status quo. You can do it from the seat you’re sitting in right now, but you must still learn to challenge well.
A BRIDGE OR A WALL
Whether you’re trying to create a new product like the Chick-fil-A milkshake or just wanting to change a system, idea, process, or tradition, challenging up requires a bridge of relationship that is strong enough to handle the weight of the challenge. Shane had the relational capital to make this withdrawal. Before you set out to challenge, you need to assess whether you’ve put in the work of relationship and if that relationship can bear the weight of the challenge you want to bring.
Here’s how it works. You see something that is befuddling. Why in the world do we do that? It makes no sense to you, and you’ve often wondered why it hasn’t been changed or challenged. You talk it over with some of your peers. You formulate a game plan. You nail down an approach to bring it up. From your perspective, the change makes total sense. And you assume your boss will see it that way as well.
The words you use when you share your idea are bricks that will either build a bridge of relationship for your idea or a wall of distrust. Since words matter, here are a few common statements and phrases you should probably avoid. This will likely require some self-control. But think about them like bricks. In what you say, are you building that bridge or are you putting up a wall?
Constantly comparing your team, organization, or church to another team, organization, or church
“Well, that church splits their middle school and high school programs.”
“It just seems like that organization is always doing something more creative with their graphics than we are.”
“Have you seen their website? It’s way easier to navigate than ours.”
Chances are, there is a church or organization doing something better than what you’re doing. And that might even be the source of your desire to change and grow and improve. There is nothing wrong with that. In fact, you should keep your eyes open to what’s happening in culture and what’s working in other organizations to foster learning and growth. But constantly comparing your church to another church is like comparing your spouse to a former relationship. It never goes well.
Emphatically declaring that what you’re doing now isn’t working
“Our small groups just don’t work. It’s basically social hour for everyone involved.”
“Kids don’t learn anything in our environments.”
Is there a better way to do what you’re currently doing? Possibly. Is the idea you have for change a better way to approach the problem? Maybe so. However, definitive statements shut down conversation. They reveal a lack of empathetic thinking, which will ultimately build a wall and not a bridge. When someone is reckless with definitive statements, it reveals a lack of discernment and creates distance in relationships. The truth is that what you’re currently doing, though probably flawed, is still working at some level. There are better ways to build your case than to speak with absolute certainty about what is currently happening. It immediately invalidates the work others are doing and questions your credibility.
Blaming the current situation on anyone, especially your boss
“This new registration system for check-in wasn’t thought through. It’s as if no one was paying attention to it.”
“No one on our team feels like they can speak up. Maybe you shouldn’t be a part of the meeting.”
Any new idea is naturally going to challenge the status quo. When you raise that new idea, you will be implicitly blaming the status quo and all of its problems on those currently in charge. Adding to that with additional statements of blame will only damage the relationship and show them you aren’t a team player and cannot be trusted. You may not directly blame someone for why something is not working, but you still want to avoid statements that imply blame or would lead your boss to question whether you have a particular individual in mind. You want to challenge with enough emotional intelligence to avoid blaming someone for what’s currently being done.
Obstinately offering an ultimatum for your future
“I just don’t know if I’ll be able to make it here if you don’t allow us to make this change.”
“If I don’t get the budget for that, I’m just not sure I can pull off the event.”
Statements like these might be true. You may not be able to survive in a culture that doesn’t allow for change. You might not be able to survive in an organization that is not willing to pay for the work or ministry it is expecting from you. You may not be able to keep your team motivated when the “they” is constantly squeezing every ounce of potential out of every opportunity. But ultimatums will rarely help you. An ultimatum eventually undermines your own leadership. Other leaders have led under far more stressful situations. Other leaders have done more with less. Other leaders have made work what you’re saying will not work. Instead of using an ultimatum to effect change, convince your boss that you are on the same team, that you are behind him or her. Make sure your boss is aware of your perspective and explore together what the implications are if the decision is or is not made. Include them in the process of evaluating, rather than presenting specific choices or actions as foregone conclusions if immediate action is not taken.
WORTH THE RISK
I know you have a burden for change. You should! And we all know that if you do not raise the challenge, there will be no change. Challenging your leader or your boss is a risk. But without the risk, there are no rewards. Remember: how well you challenge will determine how much you change.
I grew up with this quote on the wall in my childhood bedroom. I read it a thousand times, but it only became personal when I decided to be courageous enough to make a change in my own life. Paul William “Bear” Bryant said, “If you believe in yourself and have dedication and pride—and never quit—you’ll be a winner. The price of victory is high but so are the rewards.”6
Victory is not just the change that takes place because you challenge up and lead when you aren’t the one in charge. The victory is also the growth that takes place when you enter this process of learning as a leader. God has grown me more through the process of challenging my bosses than just about anything else at work. I’ve prayed more, found more humility, developed more courage, and allowed God to build my confidence in him because of these moments of challenge.
And hopefully you’re still with me, because this is such an important aspect of leading when you aren’t in charge. We’re going to take one more chapter to look at what it means to challenge up. In the next chapter, I’ll unpack the four most essential ingredients to the art of doing this well.
CHAPTER 9
BREAKING DOWN CHALLENGING UP
Every once in a while, I’ll prepare some kind of food dish and post it to social media. In theory, I disagree with the practice of posting pictures of food. Honestly, I think we’re going to look back as a society at the insanity of everyone posting about food and we’ll see it for the absurdity that it truly is. But until then, I’ll admit I’m as guilty as anyone. I don’t like it about myself, but yes, I’m a food-photo-poster. Too often, I think to myself before posting, “Ehrma ghertness. That looks delicious. Everyone needs to see this.”
Naturally, someone will say to me, “Oh, I didn’t know you like to cook.” The comment always strikes me as odd, because I don’t consider myself someone who likes to cook. I bake. I grill. I don’t really cook. And I don’t really bake or grill because I like baking or grilling. I do enjoy it, but that’s not why I do it. I bake and I grill because of one simple reason: I love food. That might be an understatement.
I have an obsession with dessert and meat. Something feels unhealthy about eating food as a hobby. But if I’m honest, eating is a hobby for me. I enjoy it as a pleasure. I enjoy it as a pastime. I think that constitutes a hobby.
The more I dabble in the kitchen, the more I have come to see the importance of quality ingredients. A few years ago, I spent every weekend for a significant number of months searching for the best chocolate chip cookie. I honestly think I’ve found it. It has everything: crispy on the outside, soft in the middle, high ratio of chocolate to dough, and a pinch of salt on the top. What I’ve found is that there are certain ingredients that just can’t be off-brand and shouldn’t be skimped in quality or quantity. For instance, if the cacao percentage in the chocolate is not sixty percent at a minimum, I’m out. And if you would like to disagree with me, I’m willing to fight. This is real, people.
In a similar way (and potentially less violent because I’m not going to blows over these), there are some ingredients in the practice of challenging up that cannot be skimped. You can’t cheat by using the cheap stuff or fake your way through this. Don’t try to replicate it with something less than authentic. These ingredients are essential, and they cannot simply be marked off of a checklist. They need to be constantly checked and monitored. They ebb and flow depending on the situation and the people involved. And if you find you’re lacking one of these ingredients, don’t try challenging up without it. Each one is a learned skill, something you can practice, and each one is an area where you can continue to grow.
THE RELATIONSHIP
As I mentioned last chapter, when you decide to challenge up, nothing is more important than the relationship you have with the person you’re challenging. Before you decide to approach your boss or even someone in another department with something potentially challenging, you need to think through the relationship you have with them. Do you get the sense they like you? Do you feel they respect you? Do they trust you?
And what about the other side of the equation? Do you like them? Do you respect them? Do they feel like you care about them? Maybe the most important question to think through before you move forward is this one: do you love your boss? You don’t necessarily need to like your boss. You might not be buddies. You might not choose to hang with them on the weekends. But you need to choose to love your boss. Loving your boss means you genuinely want what’s best for them and you’re trying to do what’s in their best interests.
Even though 1 Corinthians 13 is widely known as the Love Chapter, I find Philippians 2 to be extremely helpful in understanding what it looks like to love someone well. Philippians 2:3–4 reads like this: “Do nothing out of selfish ambition or vain conceit. Rather, in humility value others above yourselves, not looking to your own interests but each of you to the interests of the others.” In other words, put yourself to the side. Choose what’s important to the other person as more important than what’s important to you. The other person is not more important than you, but act as if they are. If you have to make a decision between what’s best for you and what’s best for the other person, go with the latter. Obviously, this is not intuitive, and it’s certainly not easy. It doesn’t always mean doing exactly what the other person wants or asks you to do. In fact, the apostle Paul gives us a little secret toward motivation and inspiration. If you want to know exactly what it looks like to do this well, whether you’re trying to love your boss, or anyone else for that matter, Paul gives us this insight in Philippians 2:5–8:
In your relationships with one another, have the same mindset as Christ Jesus:
Who, being in very nature God,
did not consider equality with God something to be used
to his own advantage;
rather, he made himself nothing by taking the very nature
of a servant,
being made in human likeness.
And being found in appearance as a man,
he humbled himself
by becoming obedient to death—
even death on a cross!
Jesus had every right to demand that everyone cater to his interests, but he didn’t do that. He had every right to take advantage of others for his sake, but he refused. He was and is valued above others, but he treated others as though they were more important. Instead of elevating himself, he poured himself out on behalf of others. He did what was best for others even when it cost him something—ultimately, his life.
Paul is saying that when you’re not sure you can love someone else more than yourself, look to Jesus. Follow his lead. Take your cues from him. In every relationship, make sure the other person is convinced of these simple truths: “I am not in this relationship for me. I am in this for you.” That’s love. And to lead well as you are relating to your boss, you have to choose to love your boss this way. If you don’t, challenging up won’t work. I cannot overemphasize how important this is. Leadership is not simply a matter of authority. Leadership is about influence. And challenging up is a form of leadership. You are leading your boss to make a decision that they might not make on their own. Choosing to love your boss is imperative if you’re trying to lead your boss. You cannot lead someone well if you don’t love them. Loving someone and leading them are a package deal. You can’t have one without the other.
So let’s say you know exactly what needs to change and you know exactly what you would like to challenge, but the relationship you have with your boss is weak. What should you do? I would suggest waiting and working on the relationship instead.
Be convinced that God put your boss in their position. Whether you like your boss or not, God establishes authority. We’ve spent most of this book looking at how to lead when you don’t have the formal authority to do so, but don’t take from this that authority is bad or useless. God created the channels of authority and God works through authority. It’s pretty clear that God is a fan of authority. God builds life under and around authority, so don’t buck against what God builds around. It’s a bad idea, and it just doesn’t work. The more convinced you are that God has appointed the authorities over you, the more responsible you will be with how you challenge them.
One of the greatest difficulties in challenging up is learning to challenge the process without appearing to challenge the person. Challenging someone personally always puts that person on his or her heels and creates an obstacle in the way of a mutually beneficial conversation. Being convinced that God establishes authority will allow you to challenge up without the sense that you’re challenging them as a person.
To build trust, practice faithfulness. Nothing will win your boss over like selfless faithfulness over an extended period of time. If you don’t yet feel like your boss trusts you because you haven’t done enough to build that trust, waiting is not wasted. Sometimes it just takes more time to show your manager that you are not in it for yourself. Do the little things to build trust. Show that you are faithful with a little so you can be trusted with a little more.
To build trust, practice faithfulness.
Our high school pastor at North Point has done this better than anyone I’ve ever met. When Darren Youngstrom stepped into his job, he had a hill to climb. Because the entire staff had turned over, many volunteers and students quit attending after losing the connection to the former leader. Darren’s first year on the job looked like failure after failure after failure. Every month, the dashboard of metrics we use to measure growth was telling a sad tale. A few of our more senior leaders felt like it was unrecoverable. They questioned whether he was cut out for the job.
I’ve noticed that too often, when things aren’t going well for someone, our instinct is to look for more weakness in that person to justify the judgment we have made in our minds. Unfortunately, it just makes matters worse and makes it even more difficult to turn the momentum around. However, I’ve watched Darren turn it around. It didn’t happen overnight, but slowly, he started winning others over through his faithfulness. I watched him pick up tasks that no one else wanted t
o pick up. He volunteered for weddings, funerals, baptisms, and tricky pastoral situations that many people dodge. He consistently delivered strong leadership in some difficult situations. And soon, the department he was responsible for began to grow. Volunteers started to buy in and so did our senior leadership. Over time, his faithfulness built trust.
Bring up disagreements when emotions are low. Jenny and I have learned that the best time to teach our kids how to obey is when the emotions are low and the consequences for disobedience are small. When the tensions are high, like when we’re rushing to get out the door or we’re stressed from a long day, that is not the best time to teach a child why obedience is so important. When it’s Saturday afternoon, one of those rare moments when life is on chill mode, we’ll have obedience practice. “Hey Lucy, let’s practice. Show me how you can go put your shoes where they should go.” And then when she does it, we dance like Justin Timberlake just asked us to be in the Tennessee Kids.
I wouldn’t try obedience practice with your boss, but I do find it helpful to employ a similar idea. When emotions are low and we’re speaking in hypotheticals, I’ve found it helpful to ask my boss this simple question, “Hey, this rarely happens, but I’m sure it will. When I disagree with something I see, what’s the best way to bring that up with you?” It’s amazing how disarming that question can be. Most people are aware that every human being is going to disagree with something from time to time. This question signals to your boss that you are thinking about those times. When you do have something you would like to challenge, you’ve already asked for permission and agreed upon the best way to handle that.
Champion publicly. Challenge privately. Over and over again, I’ve made the mistake of challenging the status quo in the wrong context and sabotaging my future ability to create change. Again, put yourself in your boss’s shoes. When you’re at your worst and someone questions or challenges you publicly, how does it make you feel? Embarrassed. Incompetent. Inadequate. What does it do to the relationship with that person? It plants seeds of doubt that you can’t trust him, that she’s not for you, and that he may even be out for your job.
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