"I've been working at the same company for a while now and have been hoping to be promoted to a lead position, but every time something comes around, I miss out. I know that I can be headstrong and I'm not afraid to speak up if I disagree with something, but this can rub people the wrong way so I think this might be why. What can I do to make sure that I still stand up for what I believe in, but also increase my chances of being promoted?"
I interpret your framing of the problem as follows:
"...I've been working at the same company for a while now..." - You believe promotion is related to time-served.
"...been hoping to be promoted to a lead position..." - You believe you are ready to lead others.
"...but every time something comes around, I miss out." - You believe you were considered (most likely because you applied or expressed interest to management) but not selected for an available leadership position at your organization.
"I know that I can be headstrong..." - You believe you can sometimes be stubborn and not open to other people's opinions.
"...and I'm not afraid to speak up if I disagree with something..." - You believe that you are fearless in expressing your objections.
"...but this can rub people the wrong way..." - You believe that you are offending others by fearlessly expressing your objections.
"...so I think this might be why." - You suspect that by fearlessly expressing your objections and thereby offending others, it is causing you to not get promoted into an available leadership position.
"What can I do to make sure that I still stand up for what I believe in, but also increase my chances of being promoted?" - You believe that standing up for what you believe in decreases your chances of being promoted into an available leadership position.
I will address each of these beliefs independently by posing them as questions:
#1 - Should I be promoted after being at a company for a certain length of time?
Not necessarily. Organizations should promote based on ability, not on tenure. That fact that many organizations value tenure over ability is one explanation for why there are so many mediocre organizations.
#2 - How do I prove to my organization that I'm ready to lead?
By already being a leader. A leader does not wait until they get a promotion to start leading. Being a leader has a simple requirement: people are following you of their own free will. If you are not leading anyone now, how can the company know that you will be an effective leader once you get promoted?
#3 - Why would management not promote someone to a leadership role when they ask for a promotion?
There can be many reasons for not getting promoted, but for a lead role, not demonstrating your leadership ability is a likely cause. Even if someone is outspoken, opinionated, contrarian, or even rude at times, if they are already the trusted leader on their team, promoting them is just a formality. Leaders often have to say what others are afraid to say, even if it's not a popular opinion. This courageousness is one of the many ways leaders earn the trust of the people that follow them: they are willing to stand up for their team even if there could be negative consequences for them personally.
#4 - Is it ever a good idea to be headstrong?
Yes - it's practically a core requirement of leadership. Having conviction is another way that leaders earn the trust of the people they lead. One way to describe someone who motivates others to accomplish a goal regardless of the obstacles is "stubborn," and that would be accurate. Remember, you're not a leader unless people are following you. Therefore, if they're following you, that means they don't mind you being headstrong. However, there is a fine line between being headstrong and ignoring the opinion of others. Good leaders don't cross that line.
#5 - Should I ever raise an objection?
Always. Never let your team march over a cliff if you can prevent it.
#6 - Does it matter if I rub people the wrong way?
Absolutely. If you bring up an objection, and you end up offending people, you were ineffective. The purpose of objecting is to persuade people that their proposed course of action is incorrect. Otherwise, you're just whining. Effective leaders know how to bring up an objection in a non-offensive way that invites everyone to weigh the pros and cons of each alternative. They also never bring up an objection without a proposal that they feel is a better choice. Good leaders don't dictate; they persuade - yet another characteristic that makes people want to follow you.
#7 - Could me raising an objection that rubs people that wrong way cost me a promotion to leadership?
It depends on the degree of how offensive you are, and how often you are offending people. Every leader loses their cool from time to time. Leadership is stressful, and leaders are humans. Most people understand that sometimes people say something they shouldn't. Provided you apologize quickly, you'll often gain forgiveness for the occasional mishap. However, if this is your standard mode of communication, it’s unlikely people will like it - even the people who want to follow you. People like to follow a calm, confident, level-headed leader, not someone who seems to be continuously frustrated while unable to communicate their frustration effectively.
#8 - Does standing up for what I believe in put me in a worse position to be promoted to a leadership position?
Absolutely not - quite the opposite. What good is a leader unless they speak the truth even if it is unpopular? What is the utility of a leader that only says what they think other people want to hear? People will decide who they want to follow regardless of who they report to in the management hierarchy. Generally, people will choose to follow people who think they have their best interests at heart. If you stand up for what you believe in and other people share your beliefs, they will want to follow you, especially if they don't feel empowered to speak up.
Here is my advice for putting yourself in the best position to get promoted to a leadership role:
Focus on leading your team without a promotion, which means your team is following you of their own free will.
Successfully lead your team to accomplish multiple objectives critical to the company.
After management has recognized the success of your team, ask how you can improve your leadership skills.
If management has no suggestions for how you can grow as a leader, ask what additional requirements remain for you to be considered for promotion.
At this point, you've started a negotiation with a lot of leverage over management - especially if the people who work for them follow you. My suspicion, however, is that they offer you a promotion long before you have to ask for it. Good leaders are rare, and if they recognize your success, they would be fools not to promote you.
Neil writes a lot more about the softer side of software development over at neilonsoftware.com. Check it out!