Jon Schaff, professor of political science, Northern State University

Grade: D (hasn’t worked well with Congress, but there’s room for improvement)

What has been the biggest surprise so far?

“I’ve been surprised at how slow the administration has been in staffing executive agencies. This might not sound like a big deal, but in government personnel is policy, and if the Trump administration wants to influence policy they need to get their people in place.”

What has been the biggest disappointment?

“In addition to the staffing issue, I’d say it’s the failure to set priorities for Congress. One of the key factors in a president’s legislative success is effectively communicating priorities to Congress.  I think if you asked a typical Republican member of Congress what three things the Trump administration wants in the first hundred days or first year, they’d struggle to tell you.”

What has been the most important moment/decision for Canada? 

“Clearly it’s the recent actions and rhetoric from the Trump administration about trade.  Whether it is lumber or dairy, the Trump administration has chosen, apparently, to pick a fight with its nearest neighbor and biggest trade partner.”

Is Ottawa's strategy for dealing with the White House effective? 

“I think it is too early to tell.  Right now the response to the trade rhetoric has been mostly counter rhetoric expressing disapproval.  We’ll have to see if Ottawa responds with actions in addition to words.  But I claim no expertise in Canadian politics.”

What is the most important U.S.-Canada issue Ottawa needs to focus on going forward?

“Clearly it is trade, as expressed above.” 

Christopher Sands, director of the Center for Canadian Studies, Johns Hopkins University

Grade: B (passing, but room for improvement)

What has been the biggest surprise so far?

“For me the biggest surprise has been the skillful way that the Trudeau government has navigated Washington during and since the U.S. election. The results have impressed other world leaders, and advanced Canadian interests well.”

What has been the biggest disappointment?

"The clumsiness of the White House team on relations with the North American neighbours over NAFTA renegotiation and some other issues. The slow pace at which the Trump administration has filled key positions (such as ambassadors to Canada and Mexico, the NSC staff director for North American Affairs, the Deputy Assistant Secretary of State for North American Affairs, the U.S. trade Representative, etc), combined with the understandable desire of the administration to get moving has hurt the Trump agenda by letting political advisors run amok – such as appears to be the case with the on-again, off-again executive order on pre-emptive NAFTA withdrawal. And easy victories such as making arrangements to host a North American leaders Summit (NALS, which it is the US turn to host) to launch NAFTA renegotiation, are quickly becoming missed opportunities.”

What has been the most important moment/decision for Canada?

“The NAFTA renegotiation is clearly the most important decision, and the fidelity of the Trump administration so far to established process (as seen in the 2017 Trade Strategy, the leaked NAFTA renegotiation draft letter, and President Trump’s rather traditional focus on issues of concern to Congress, rounding up congressional support for the negotiation issue by issue and district by district). This is a counterpart to my disappointment, but my hope is that this procedural attention to detail will prevail in shaping administration policy.”

Is Ottawa’s strategy for dealing with the White House effective?

“Yes, to a point. The slow pace of staffing in the administration has forced Canada to cultivate ties to White House insiders and Trump himself. However, as the administration fills out a full staff complement and issues grind down to a detailed level, Canada will need to shift to a lower tier of officials. Key in this is the U.S. Ambassador in Ottawa, who either adds value or will be quickly bypassed.”

What is the most important U.S.-Canada issue Ottawa needs to focus on going forward?

“The NAFTA renegotiation is the most important issue, although I could just say trade. Losing market access will damage Canada’s ability to attract FDI, and cruelly will also hurt Canada’s chances of successfully concluding agreements with other major trading partners. The CETA is nice, but the European economy is wobbly. The TPP is good, but less so without the United States, and China and Japan are slowing down, with South Korea rattled by its neighbour and the recent impeachment of its president. There simply is no substitute for the U.S. market, and Canada needs a deal that keeps the essential market access provisions of NAFTA in place.”

Maryscott Greenwood, chief executive officer, Canadian American Business Council

Grade: E (for an incomplete term)

What has been the biggest surprise so far? 

“We are pleasantly surprised that the Trump Administration is acknowledging the importance of the integrated nature of the economy in North America.”

What has been the biggest disappointment? 

“We are disappointed in the strong anti-trade, protectionist rhetoric that has emerged over the course of the campaign and transition.”

What has been the most important moment/decision for Canada? 

“Canada's decision to engage with the Trump Administration in a constructive way, highlighting the importance of the Canadian economy to U.S. jobs and economic prosperity has been a key strategic move by the Trudeau government.”

Is Ottawa's strategy for dealing with the White House effective? 

“So far, so good.  Decreasing the temperature, and fighting bombastic rhetoric with a steady stream of facts is having a positive effect.

What is the most important U.S.-Canada issue Ottawa needs to focus on going forward? 

“The U.S. and Canada need to remind ourselves every day that we are in this together and that the biggest economic and security threats we face are common to both of us.”

David Wilkins, former U.S. ambassador to Canada

Grade: A (Supreme Court appointment, KXL approval, roll back of restrictive regulations on businesses, excellent national security team)

What has been the biggest surprise so far?

“One of the things I’ve been most surprised with is how he’s reached out to Congress — meetings, dinners, etc. In the end, that will pay off.”

What has been the biggest disappointment?

“The Congress not being able to come together on repeal of Obamacare, but I’m optimistic [that it will be repealed in the future].”

What has been the most important moment/decision for Canada?

“Keystone XL pipeline approval.”

Is Ottawa’s strategy for dealing with the White House effective?

“I think the Prime Minister has been very good at keeping the lines of communications open and sending  cabinet members to Washington. I think the Trudeau government has effectively used many people to get the message out about the importance of U.S-Canada relationship. There’s obviously a very concerted effort emphasizing the importance of that relationship.”

What is the most important U.S.-Canada issue Ottawa needs to focus on going forward?

“Based on developments this past week – the obvious one would be trade. More specifically NAFTA trade and softwood lumber negotiations.”

*Some answers were shortened for the sake of brevity