How to challenge more senior leaders

In several past articles (here, here, and here), I’ve discussed the theme of how leaders can challenge, push or pull team members towards a difficult goal, even to the limit of performance, but in ways that don’t break them (i.e., fracture relationships, or dismantle motivation).

You might think challenging others is a straightforward task for leaders. After all, in corporate settings where I most often work, executives sitting in leadership positions possess more power than most of their colleagues. The hierarchical structure of large institutions means there are more people at the bottom of the pyramid than the top. You’d assume leaders/executives at upper echelons spend most of their time challenging ‘downwards’ to those in subordinate positions, who may be highly motivated to comply based on their power disadvantage.

But the sobering reality of life inside executive roles is far more complex. Even senior executives often spend considerable time influencing ‘upwards,’ to their boss, to more senior officers of the company, or to Board members.

The prospect of challenging ‘upwards’ introduces a complex set of risks. It’s one thing to ask your direct report to do more, or better, but it’s another to encourage the same to someone who holds the power to punish you in subtle or substantial ways. Issue the wrong kind of challenge and, best case, you could receive a verbal reprimand. In more severe cases, consequences could involve withholding career opportunities (e.g., special projects, promotions), restricting your salary or bonus, or denting your reputation by making negative comments about you to others. In addition, they may have their own eccentricities which could render the interaction unpredictable. They may be sensitive, egocentric, or highly attuned to the perception that they’re not ‘in charge.’ They may lash out for perceiving (however unintentional) that you’re embarrassing or criticizing them by challenging their ideas or positions. They may say they want your input but react in unexpected ways when you offer it.

Although challenging upwards is delicate and difficult, it’s also a skill that’s necessary for leadership effectiveness – at all levels. In this article, I’ll outline strategies leaders can use when they face the inevitable but intimidating task of challenging upwards. In particular I’ll define what I mean by ‘challenging,’ explain several preparatory steps to take before challenging someone more senior, and summarize twenty-two strategies leaders can use to maximize the impact of an upward challenge.

What do I mean by ‘challenge’?

When I use the phrase ‘challenge’ you might think I’m referring to telling someone that they’re wrong or contradicting them. That’s not exactly what I’m getting at. Rather I mean suggesting to someone who has more power, status, or title than you, in compelling ways, that there’s a higher performance standard that they should reach for.

What could this look like?

1. It could involve challenging for the peak or limit of performance, a maximalist state equivalent to giving absolutely everything you can on a goal or objective.
2. It could involve challenging to do something better, in the spirit of continuous improvement.
3. It could involve challenging to be ‘the best’ at something, to achieve excellence relative to others.
4. It could involve challenging to seek a change from the status quo, to do something different than how it’s been done.
5. It could involve challenging to seek some sort of competitive advantage relative to others.
6. Finally, it could also involve challenging to do something that creates ‘value’ for the team, or company (however you define ‘value’).

Get your ducks in a row

Before thinking about challenging upwards, you may want to consider if the conditions are right to do so.  

To determine if the time optimal, ask yourself several questions:

1. Do I understand the context (including people, issues/facts, and the business)? Leaders should educate themselves about the more senior person or people involved in the meeting in which they plan to challenge, so they can tailor their approach to their audience. They should also ensure they’ve ‘done their homework’ on the substantive issue they’re challenging on, otherwise any perceived ignorance will undermine their case. Finally, they should ensure they understand the broader business dynamics (e.g., how the company runs and operates, both internally and as part of the external industry/market) that their challenge is situated within. (Note that knowing all this context makes upward challenging much harder for newcomers to a company.)
2. Do I have credibility in the eyes of the more senior leader? Credibility usually constitutes perceived expertise and experience in the area you’re about to challenge on.
3. Do I have a strong relationship with the more senior person I’m challenging? Relationship quality, probably more than anything else, will shape how your challenge is received. High quality relationships will enable greater leeway when challenging, and reduce the chances of causing offence.
4. Is the culture open to challenging? In this culture, are juniors given the freedom to challenge upwards? Is it an atmosphere that’s conducive to sharing power across levels? Is there a sense of psychological safety?
5. Do I have allies? It may be important to align with other key allies first – essentially coalition-building - before challenging upwards. Doing so, and then broadcasting that alliance to the more senior leader during the challenge, will exert social pressure on them to migrate towards your position.
6. Am I financially secure? (Yes, I’m serious.) Older and experienced leaders are more comfortable challenging, in part based on their credibility, but also because they don’t need their next pay cheque to service their mortgage. They have some financial security. They don’t fear losing their job as a result of challenging powerful actors and ‘speaking truth to power.’ Before challenging upwards, consider if you’re ready to risk possible financial penalty, or whether you have enough perceived credibility and financial security to buffer you through the experience.

Strategies for challenging upwards

You’ve got your ducks in a row. You’ve completed your prework. Now let’s open the playbook and unveil the strategies you might use to challenge upwards.

1. Alignment/Shaping conversation: This involves aligning on the context, assumptions, and mental models involved in the situation. Do you and the other party see the world (and especially the issue you want to challenge about) in a similar way? Determining this involves exploratory conversations, and could be a preparatory step you take before challenging, or a follow up discussion after a challenge misses the mark and you sense a need to recalibrate. This may involve answering many senior leader questions just to 'get on the same page.'
2. Anchoring: This involves aligning the challenge/push/pull with something bigger than you or your personal agenda. For example, you can anchor the challenge to higher order principles (“this is the right thing to do”), to company values (“this aligns with our ‘doing what's right’ value”  [or some other value]), or to the vision of the company (“we have a vision to be a sustainable company, and what I'm challenging for is aligned with that”). You could also anchor your challenge to the leader's goal (“you said you wanted to achieve an increase in profit this year, and this helps to do that”). The idea here is to depersonalize the request, make it not about you, or your ego, or your personal agenda, and to show how what you're pushing for aligns with the collective's best interest.
3. Appealing to self-interest: This involves describing how what you're pushing for personally benefits the senior leader you're trying to influence. This is the old 'what's in it for me' approach. Lay out all the positive benefits that will personally accrue to the senior leader you’re challenging, if they align with you.
4. Asking questions: This involves asking questions in multiple ways that poke, nudge, and needle the senior leader towards your goal. Questions can take many forms, ranging from less to more assertive, or ‘soft’ to ‘hard’ in tone. For example, ‘soft’ questions tend to be exploratory, and involve seeking clarity, uncovering detail, or building understanding of a complex problem. ‘Soft’ questions are more likely to involve open-ended phrasing, which leads to two-way dialogue. ‘Hard’ questions by contrast are provocative and direct, less encumbered with a ‘warm and fuzzy’ relational tone. They can involve challenging a core position or assumption, or testing others' understanding or knowledge. ‘Hard’ questions more often involve stating a position, then asking others to confirm or refute it, which generates more debate than dialogue. The key idea here is to use different kinds of questions to move the conversation towards aligning with your challenge.  
5. Assertion: Challenging other people necessitates some minimum level of assertion, and a willingness to influence others to your way of thinking. There are two kinds of assertion, positive and negative. 'Positive assertion' involves showing courage to ask for what you want, speaking your mind, pushing the limits of the discussion, and being persistent in calling out the need for improvement. Think about this as playing 'offense’ with assertion. 'Negative assertion' involves holding a boundary, or a line, or to a rule, or pushing back against a position you disagree with. Think about this as playing 'defense.’ Both might be needed when challenging a more senior leader.
6. Capitalizing on failure: This involves using an obvious 'failure' incident to advocate for change. The idea is that people's assumptions about how to do things become 'unfrozen' or 'fluid' after a failure, and you can use that moment to say “what we were doing - the status quo - hasn't worked here. It’s plain as day, we can’t hide from it. We must change the way we approach this problem. Now, everything is up for debate and reconsideration. With that in mind, I'm proposing a different approach, and now is the time to try it.”
7. Creating discrepancy: This involves making the more senior executive feel the tension associated with the gap between 'where they are now' and 'where they want to be'. For example, you could say "your goal is X, but our current strategy will never get us there - there's a discrepancy between your goal and our strategy." Another way to say it could be "our current goal is at risk if we continue to use this status quo strategy – so we need to change." The idea here is to compel the decision maker feel discomfort or tension or even anxiety due to facing the growing gap between current reality, and where they want to go. If you can get the senior leader to feel that discrepancy, they will become more motivated to close the gap, and to listen to any solutions/ideas (like yours) that facilitate that closure. 
8. Credible social proof: This involves sharing practices or recommendations from other credible sources (e.g., “here are other companies that we like to compare ourselves to, who are using the practice I’m advocating for”). (Note that the prework step ‘Building Allies’ mentioned above is also a form of social proof – if the senior leader trusts your allies, and they align with your challenge, that senior leader will see their support as validation or ‘proof’ that your position is correct.)
9. Controlling emotion: Feel free to debate me on this, but several leaders I’ve spoken with over the years have suggested to me that controlling emotion was critical when challenging more senior decision makers. One reason for this could be that the presence of emotion is frowned upon, seen as unprofessional, or as an indicator of irrationality at executive levels (though this may depend on the organizational culture). Another possible reason could be that challenging in an emotional way may be seen as less respectful or deferential to the more senior leader. To be conservative, you might try to stick to a calm delivery that suggests your challenge is thoughtful and rational. (Paradoxically, the reverse of this principle might be true for leaders challenging ‘downwards’: their expressions of emotion may be more often viewed as positive, charismatic, or inspirational.)
10. Focusing attention: This involves trying to orient the attention of the senior leader towards a specific area you think is important. Remember, those living in the executive world exist in a rarefied reality. They have zero time, are under constant demands and pressure, and are perpetually looking to economize. You might forgive them, despite being intelligent, for struggling to capture all the nuances embedded in your challenge. You need to help them focus on key parts of your message. For example, you could make a bold and provocative statement to get their attention, you could ask for improved attention on a specific issue (“I need you to focus on this part”), or you could ask them to direct their attention to a critical area of underperformance (“we are struggling here, and you need to be aware of it”).
11. Framing: This involves framing any challenge that you make as 'reasonable.'
12. Making the case: This involves explaining or reiterating your rationale, including 'the need,' and giving numerous reasons why your position is valid/persuasive.
13. Moral imperative: This involves challenging for what you define as 'right,' or using a belief in what's 'right' as a justification for pushing. This approach invokes a sense of obligation and duty to comply with the challenge you’re making. “This is not just good for the business, this is the ‘right’ thing to do, and we have a duty and obligation (to shareholders, to customers, to the broader stakeholder community) to do this.” 
14. Offering a solution/plan: Even though this is cliché by now, I need to mention this principle because so many executives I speak to reference it. When challenging/pushing/pulling ‘upwards’ you can't just offer a critique, you also need to propose a credible solution/proposal. I believe this is important because it removes cognitive burden from the more senior leader (they don’t have to generate the solution themselves), and allows the senior leader to feel competent by making a quick yes/no decision based on what you’ve proposed.
15. Outlining costs of status quo: This involves pointing out the costs of NOT changing, or the downside of doing nothing. Here a leader could say “you may think sticking to the status quo is safe, but in fact it’s risky, and if we continue to adhere to it all these bad things will happen (proceed to list many bad things).” (As an aside, I find executives often speak the language of 'cost' and 'risk,' and since this point targets both these themes, it should resonate with them.)
16. Pacing: This involves challenging/pushing/pulling in a way that you don't need immediate closure. It involves giving the other party space to think after their initial interaction. It means challenging in a distributed way, over time, across several interactions. Adopting this style requires accepting that challenging is a process which can have a cumulative effect, and that it's not just a ‘one time’ event.
17. Showing respect and deference: This involves showing respect, deference and some humility when challenging upwards. For many of the leaders I work with, this often takes the form of reassuring more senior executives that “this is just my position, and of course whatever you decide I will support.” 
18. Staying positive: This involves avoiding negativity in the interaction, like saying 'no', or 'this isn't possible,' or 'you're wrong.' Most senior executives are not used to hearing a direct, negative refutation from a more junior person.
19. Suggesting an alternate path (to the leader’s goal): If a leader is focused on achieving a singular goal, but the current strategy won't reach that goal, you can offer an alternative path for the leader to still reach their cherished objective. This involves saying something like “we thought we had a path to success, but that no longer works for us; however we can still get to where you want to go, using a path that you weren't aware of previously… let me explain...” 
20. Tailoring approach: This involves challenging the more senior leader you’re interacting with in a bespoke way, and can take several forms. First you can tailor your ‘challenge style’ based on the idiosyncratic preferences of the more senior leader. Some need more respect and deference in interactions, others will tolerate more directness. Some will value facts most, others may be open to ‘intuitive’ or ‘gut feel’ data points.  Some leaders may want to decide on the spot, while others will need some ‘soak’ time to process. Tailoring might also involve adjusting to the situational dynamics you face. For example, if the senior leader is unaware of key details, you may need to spend more time in ‘educational dialogue’ mode before issuing your challenge. Finally, tailoring might involve shaping any proposed alternative paths to success in a way that fits the preferences of the leader. For example, if the more senior leader is conservative by nature, then challenging them to consider the most conservative of three alternative paths you’ve identified may be wise.
21. Turning up the signal: When you don't feel your 'signal' or message is getting across (maybe the senior leader is trying to digest many competing or confusing bits of information), one option is to turn up the signal strength. You could add more emphasis, increase animation or volume as you talk, or escalate the tone/directness/intensity of the challenge to help the leader attend to your message. (This tactic bears some similarity to ‘Focusing Attention’ as described in #10 above.)
22. Using data/evidence/facts: Michael Bloomberg (founder and former CEO of Bloomberg, and former Mayor of New York) once said: “In God we trust. All others bring data.” This might be the most important principle in this list. Facts>opinion when it comes to challenging upwards to a senior executive audience. One executive once told me "when you use facts and data to make your case upwards, I don't know that I've ever seen it go wrong." 

Receiving challenge

To this point we’ve focused more on the junior ‘challenger’ than the senior leader recipient. Although the ‘challenger’ needs a deft touch when pushing upwards, the senior leader bears an even larger responsibility to create an environment that’s conducive to upward pushing. They have the unique power to remove barriers to upward challenging. They can shape the culture and norms of the team, such that everyone understands upward challenging is expected and supported. They can provide the reassurance that juniors shouldn’t fear punishment or reprisal for pushing them.

One way senior leaders can reduce barriers to challenging is by structuring team interactions in ways that account for neurodiverse people. For example, senior leaders can give the team 24 hours to ‘process’ some important information, before asking members to push back on it. This allows both the fast-processing, often extraverted ‘I want to debate and challenge this right now!’ people to contribute, but also gives the slower-processing, more introverted folks time to organize their thinking and assemble their challenge.

Finally, it’s important to remember that great leaders should want to be challenged from the bottom up. It’s impossible for executives to know everything that’s going on within the many organizational layers beneath them. Though they are accountable for that activity, it would be impossible and foolish of them to try to track or control all of it. So, they rely on their staff to tell them when they’re missing something important, and to provide them feedback about what’s happening within the dark, dank engine rooms of the business. Great leaders are open to hearing all the reasons why they could be wrong. They know that regardless of the opinions or facts swirling about, they get to make the final decision, and so they want all the raw material available to do that well. Great leaders not only give challenge, but they show openness and receptivity to receiving it as well.

Conclusion

This discussion of challenging upward reveals several lessons – like leadership can originate from anywhere, it can travel in multiple directions, and it may exist independent of the position power accompanying it. The most important lesson of all, however, may be that challenging upward reminds us to confront a stereotype about leadership, that the leader sits atop a hill, alone, all powerful. As we have seen, great leaders are not isolated or insular, rather they compromise their power constantly in service of listening to and learning from those around and below them. They allow their views to be challenged, because they recognize the humanity and vulnerability in their thinking, that they are fallible, biased, and blind to what others can see. In the end, great leaders know they don’t need all the answers, because given the chance, many of them will bubble up from below.

Thank you for reading.

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As always I would welcome your feedback on anything you read, and I would love to learn from your perspective. To share your thoughts, you can leave a comment at the end of the article, or if you prefer you can also email me your feedback at tjackson@jacksonleadership.com.

Tim Jackson Ph.D. is the President of Jackson Leadership, Inc. and a leadership assessment and coaching expert with 18 years of experience. He has assessed and coached leaders across a variety of sectors including agriculture, chemicals, consumer products, finance, logistics, manufacturing, media, not-for-profit, pharmaceuticals, healthcare, and utilities and power generation, including multiple private-equity-owned businesses. He's also worked with leaders across numerous functional areas, including sales, marketing, supply chain, finance, information technology, operations, sustainability, charitable, general management, health and safety, quality control, and across hierarchical levels from individual contributors to CEOs. In addition Tim has worked with leaders across several geographical regions, including Canada, the US, Western Europe, and China. He has published his ideas on leadership in both popular media, and peer-reviewed journals. Tim has a Ph.D. in organizational psychology, and is based in Toronto.

Email: tjackson@jacksonleadership.com

Web: www.jacksonleadership.com

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